Pyrimidine derivatives, herbicides and plant growth regulators

ABSTRACT

Novel pyrimidine derivatives of the formula (I): ##STR1## wherein R1 is a C 1  -C 6  haloalkyl group, a C 1  -C 6  alkyl group, a C 3  -C 6  cycloalkyl group or the like, R2 is a hydrogen atom, a C 1  -C 6  alkyl group, a C 3  -C 6  cycloalkyl group or the like, and X is a carbonyl group or --C(R3)OH (wherein R3 is a hydrogen atom, a C 1  -C 6  alkyl group or the like).

This is a 371 of PCT/JP94/01311 filed Aug. 9, 1994.

TECHNICAL FIELD

The present invention relates to novel pyrimidine derivatives, andherbicides and plant growth regulators containing such derivatives asactive ingredients. The derivatives are also useful as intermediates formedicines and agricultural chemicals.

BACKGROUND TECHNIQUE

It has not been known at all that the group of compounds of the presentinvention which contain a pyrimidine ring having hydrogen atoms at the2- and 6-positions and having specific substituents introduced at the 4-and 6-positions exhibit a herbicidal activity and a plant growthregulating activity. Further, none of their chemical structures have notbeen known except that those of three compounds,4-methyl-5-acetylpyrimidine, 4-tert-butyl-5-tert-butylcarbonylpyrimidineand 4-phenyl-5-benzoylpyrimidine, are disclosed in Journal ofHeterocyclic Chemistry, Vol. 20, 1983, p. 649.

In order to protect important crop plants such as rice, soybean, wheat,corn, cotton and sugar beet and increase their productivities, manyherbicides have been put in practical use so far. These herbicides areroughly classified into three categories, those for upland fields, forpaddy fields, and for non-agricultural fields, according to theapplication site. Further, each category can be classified as a soilincorporation type, a pre-emergence soil treatment type and apost-emergence treatment (foliage treatment) type, according to themanner of application.

With the recent global population explosion, the productivities ofimportant crop plants will undoubtedly affect the food economy of eachcountry. These changes will be inevitably accompanied by changes of theconventional mode of agriculture toward the 21st century. Actually,development of herbicides which can economically and effectively kill orcontrol weeds detrimental to the growth of crop plants, is becoming moreand more important to farmers than ever.

As such herbicides, chemicals which meet the following requirements aredesired to be developed.

Those having high herbicidal effects at low doses (it is necessary tokill weeds at as low doses as possible from the viewpoint ofenvironmental protection), those having adequate residual activities(since a problem that soil-persistent chemicals damage next crops hasarisen recently, it is important to show an adequate residual activityafter application), those which promptly kill weeds upon application (itis possible to sow or transplant next crops soon after chemicaltreatment), those which do not require frequent treatment (it isimportant for farmers to minimize the frequency of cumbersome weedcontrol operations), those intended to control a wide range of weeds(chemicals capable of controlling a variety of weeds having differentproperties such as broad-leaves weeds, graminaceous weeds and perennialweeds independently, are desirable), those which can be applied byvarious methods (a stronger herbicidal effect can be obtained bycombining an effect of soil treatment, an effect of foliage treatmentand so on), and those which do not show any problematic phytotoxicityagainst crop plants (in a field where a crop plant coexists with weeds,those capable of selectively killing weeds are desired), are preferred.However, no existing herbicides satisfy all of these requirements.

On the other hand, diseases and insect pests, which are a hindrance tofarmers in crop cultivation, are effectively controlled by excellentfungicides and insecticides. However, in addition to these harmfulorganisms, there are other factors which lower the yield and thequalities. For example, wind or rain lodges barley, rye, wheat, rice,corn, soybean or cotton at time of harvesting. One of the easiest andmost effective preventive measures is to suppress internode elongationfor the purpose of preventing lodging of these crop plants, andtherefore development of growth retardants which have no influence onyield is becoming more and more necessary than ever. As such growthretardants, chemicals which meet the following requirements are desiredto be developed.

Those having high dwarfing effects at low doses (especially from theviewpoint of environmental protection, it is necessary to exhibitdwarfing effects at as low doses as possible), those having adequateresidual effects (it is important that the residual amounts in soilafter application are small), those which act moderately (a suddenaction is not desirable), a chemical treatment is preferred to beconducted once, basically (it is important for farmers to reduce thefrequency of cumbersome operations), those which can be applied byvarious methods (it is possible to select an appropriate applicationmethod for a crop, from soil treatment, foliage treatment, seedtreatment and so on), it is preferred to inhibit foliage growth for thepurpose of translocation of nutrients to flowers or fruits rather thanto foliage (which leads to increase in the yield). Further, those havinglittle growth retarding effects on roots are preferred.

On the other hand, there is a desire for uses in inhibiting the growthof lawn grasses, controlling fruit tree turions, dwarfing ornamentplants for the purpose of high commercial values, suppressing the growthof hedge plants and controlling a flowering time. Since complete deathof weeds in a non-agricultural field causes run-off of the soil, inrecent years it is necessary to control weed length and avoid killingthem.

DISCLOSURE OF THE INVENTION

The present inventors have conducted extensive researches on theherbicidal action and the plant growth regulating action of the novelpyrimidine derivatives under these circumstances. As a result, theyfound that pyrimidine derivatives of the following formula exhibitremarkable herbicidal activities and plant growth regulating activities.The present invention has been accomplished on the basis of thisdiscovery. Namely, the present invention provides a novel pyrimidinederivative of the formula (I) (hereinafter referred to as the compoundof the present invention): ##STR2## wherein R1 is a C₁ -C₆ haloalkylgroup, a C₁ -C₆ alkyl group, a C₃ -C₆ cycloalkyl group, a C₃ -C₆halocycloalkyl group or an optionally substituted phenyl group (whereinthe substituent is selected from the group consisting of a halogenatoms, a C₁ -C₄ alkyl group, a C₁ -C₄ alkoxy group, a C₁ -C₃ haloalkylgroup, a C₁ -C₃ haloalkoxy group and a phenyl group), R2 is a hydrogenatom, a C₁ -C₆ alkyl group, a C₃ -C₆ cycloalkyl group, a C₃ -C₆cycloalkyl(C₁ -C₄)alkyl group, a C₁ -C₆ haloalkyl group, a C₃ -C₆halocycloalkyl group, a C₃ -C₈ alkenyl group, a C₃ -C₈ alkynyl group, aC₁ -C₂ sulfonyl(C₁ -C₄)alkyl group, a C₁ -C₄ alkylthio(C₃ -C₆)cycloalkylgroup and an optionally substituted phenyl group (wherein thesubstituent is selected from the group consisting of a halogen atom, aC₁ -C₄ alkyl group, a C₁ -C₄ alkoxy group, a C₁ -C₃ haloalkyl group, aC₁ -C₃ haloalkoxy group and a phenyl group), X is a carbonyl group or--C(R3)OH (wherein R3 is a hydrogen atom, a C₁ -C₆ alkyl group, a C₃ -C₈alkenyl group, a C₃ -C₈ alkynyl group or an optionally substitutedphenyl group (wherein the substituent is selected from the groupconsisting of a halogen atom, a C₁ -C₄ alkyl group, a C₁ -C₄ alkoxygroup, a C₁ -C₃ haloalkyl group, a C₁ -C₃ haloalkoxy group or a phenylgroup) (provided that when the carbon atom is an optically active carbonatom, the lacemate and both of the two isolated optical isomers areincluded)!. The present invention also provides herbicides and plantgrowth regulators containing the compounds of the present invention.

Some of the compounds of the present invention exhibit high herbicidalactivities as a herbicide for upland fields and non-agricultural fields,either in soil treatment or in foliage treatment at low doses againstbroad-leaved weeds such as Solanaceous weeds (Solanaceae) represented byblack nightshade (Solanum nigrum) and jimsonweed (Datura stramonium),Malvaceous weeds (Malvaceae) represented by velvetleaf (Abutilontheophrasti) and prickly sida (Sida spinosa), Conolvulaceous weeds(Convolvulaceae) presented by morningglories (Ipomoea spps.) includingcommon morningglory (Ipomoea purpurea) and bindweeds (Calystegia spps.),Amaranthaceous weeds (Amaranthaceae) represented by livid amaranth(Amaranthus lividus) and redroot pigweed (Amaranthus retroflexus),Composite weeds (Compositae) presented by common cocklebur (Xanthiumpensylvanicum), common ragweed (Ambrosia artemisiaefolia), sunflower(Helianthus annuus), hairy galinsoga (Galinsoga ciliata), creepingthistle (Cirsium arvense), common groundsel (Senecio vulgaris) andannual fleabane (Erigeron annus), Cruciferous weeds (Cruciferae)represented by India field cress (Rorippa indica), kedlock (Sinapisarvensis) and shepherd's purse (Capsella bursapastoris), Polygonaceousweeds (Polygonaceae) represented by posumbu knotweed (Polygonum blumei)and wild buckwheat (Polygonum convolvulus), Portulacaceous weeds(Portulacaceae) represented by common purslane (Portulaca oleracea),Chenopodiaceous weeds (Chenopodiaceae) represented by common lambsquater(Chenopodium album), figleaved goosefoot (Chenopodium ficifolium) andkochia (Kochia scoparia), Caryophyllaceous weeds (Caryophyllaceae)represented by common chickweed (Stellaria media), Scrophulariaceousweeds (Scrophulariaceae) represented by persian speedwell (Veronicapersica), Commelinaceous weeds (Commelinaceae) represented by asiaticdayflower (Commelina communis), Labiate weeds (Labiatae) represented bydead-nettle (Lamium amplexicaule) and red deadnettle (Lamium purpureum),Euphorbiaceous weeds (Euphorbiaceae) represented by prostrate spurge(Euphorbia supina) and spotted spurge (Euphorbia maculata), Rubiaceousweeds (Rubiaceae) represented by bed straw (Galium spurium) and indianmadder (Rubia akane), Violaceous weeds (Violaceae) presented by violet(Viola mandshurica), and Leguminous weeds (Leguminosae) represented byhempsesbania (Sesbania exaltata) and sicklepod (Cassia obtusifolia), andvarious cropland weeds such as Graminaceous weeds represented byshattercane (Sorgham bicolor), fall panicum (Panicum dichotomiflorum),johnsongrass (Sorghum halepense), barnyardgrass (Echinochloa crus-gallivar. crus-galli), barnyardgrass (Echinochloa crus-galli var. praticola),barnyardgrass (crop) (Echinochloa utilis), large crabgrass (Digitariaadscendens), wild oat (Avena fatua), goosegrass (Eleusine indica), greenfoxtail (Setaria viridis) and water foxtail (Alopecurus aegualis), andCyperaceous weeds represented by purple nutsedge (Cyperus rotundus,Cyperus esculentus).

Further, the compounds of the present invention exhibit high herbicidalactivities as a herbicide for paddy fields either in submerged soiltreatment or in foliage treatment at low doses against various paddyweeds such as Alismataceous weeds (Alismataceae) represented by narrowleaf waterplantain (Alisma canaliculatum), arrowhead (Sagittariatrifolia) and japanese ribbon wapato (Sagittaria pygmaea), Cyperaceousweeds (Cyperaceae) represented by smallflower umbrellaplant (Cyperusdifformis), perennial flat sedge (Cyperus serotinus), bulrush (Scirpusjuncoides) and water chestnut (Eleocharis kuroquwai), Scrophulariaceousweeds (Scrothulariaceae) represented by false pimpernel (Lindemiapyxidaria), Potenderiaceous weeds (Potenderiaceae) represented byducksalad (Monochoria vaginalis), Potamogenaceous weeds(Potamogetonaceae) represented by roundleaf pondweed (Potamogetondistinctus), Lythraceous weeds (Lythraceae) represented by toothcup(Rotala indica), barnyardgrass (Echinochloa oryzicola), barnyardgrass(Echinochloa crus-galli var. formosensis) and barnyardgrass (Echinochloacrus-galli var. crus-galli).

Further, the compounds of the present invention are found to have a highlevel of safety for important crop plants such as rice, wheat, barley,sorgo, peanut, corn, soybean and cotton and sugar beet.

Some of the compounds of the present invention can be used as a plantgrowth regulator for upland fields, paddy fields or non-agriculturalfields, in soil, foliage or seed treatment, to inhibit of growth orelongation of broad-leaved weeds such as black nightshade, jimsonweed,velvetleaf, prickly sida, common morningglory, livid amaranth, redrootpigweed, common cocklebur, common ragweed, sunflower, hairy galinsoga,creeping thistle, common groundsel, annual fleabane, India field cress,kedlock, shepherd's purse, posumbu knotweed, wild buckwheat, commonpurslane, common lambsquater, figleaved goosefoot, kochia, commonchickweed, persian speedwell, asiatic dayflower, dead-nettle, reddeadnettle, prostrate spurge, spotted spurge, bedstraw, indian madder,violet, hempsesbania, sicklepod and hairy beggarticks, graminaceousweeds such as shattercane, fall panicum, johnsongrass, barnyardgrass,blackgrass, large crabgrass, wild oat, goosegrass, green foxtail andwater foxtail, cyperaceous weeds such as purple nutsedge, and variouspaddy weeds such as narrowleaf waterplantain, arrowhead, japanese ribbonwapato, smallflower umbrellaplant, perennial flat sedge, bulrush, waterchestnut, false pimpernel, ducksalad, roundleaf pondweed, toothcup,barnyardgrass, and inhibit growth of these weeds without complete deathof plants, which may cause soil erosion.

The compounds of the present invention can be used to prevent lodging,inhibit the elongation, strengthen stems, thicken stems, prevent spindlygrowth, shorten stems and shorten internose of crop plants such as rice,wheat, barley, rye, corn, soybeans, peanut, cotton, sunflower, sugarbeet, potato, rape and sugar cane, and consequently they are expected tolead to increased crop yields and improved resistance to badenvironments and diseases and insect pests. Further the compounds of thepresent invention can be used to inhibit lawn grass growth, and areuseful for dwarfing ornamental plants, indoor plants, garden plants orgreenhouse plants.

The compounds of the present invention can be used to inhibit a woodyplant from growing or bearing flowers. For example, they are used forkeeping a hedge in shape, controlling the shape of a fruit tree (forexample, apple, pear, cherry, peach, grapevine and western pear), ormaking pruning less necessary. Further, the compounds of the presentinvention can be used for flowering time control, branching control orstimulation of axillary bud growth through destruction of apicaldominance.

Recently, a social problem of hay fever that pollens of cedar andJapanese cypress pollens induce city people's allergy has emerged. Useof the compounds of the present invention make it possible to inhibitand control flower bud formation and flower bearing of cedar andJapanese cypress which are responsible for hay fever. Pre-emergence seedtreatment at a low dose may stimulate germination. In this case, theyexert an initial growth stimulation action without inhibitinggermination or elongation.

Therefore, the compounds of the present invention can be used as anactive ingredient of herbicides and plant growth regulators for uplandfields, paddy fields, lawns, orchards, pastures and othernon-agricultural fields. Now, various methods for producing them will bedescribed in details.

The compounds of the present invention can be synthesized by the methodsrepresented by the following Scheme 1 to 3 (in Scheme 1 to 3, R1 to R3are as defined above, each of Ra and Rb is a C₁ -C₃ alkyl group, Met isa metal atom such as Mg or Zn, and Hal is a halogen atom).

The starting material, 2,4-dicarbonyl compound (II), can be easilysynthesized in accordance with the methods disclosed in The Chemistry ofthe Carbonyl Group, p. 273, written by D. P. N. Satchell and R. S.Satchell, edited by Saul Patai (published by Wiley-interscience, 1966)and Organic Reactions Vol. 1, p. 266, written by C. R. Hauser and B. E.Hudson, Jr. (published by John Wiley & Sons, Inc., 1942). ##STR3##

(1) Synthesis route (1) in Scheme 1 indicates a method of producing apyrimidine derivatives (V) of the present invention (wherein X: C═O),which comprises reacting a 2,4-dicarbonyl compound (II) with anorthoformic ester derivative and then reacting the resulting 3-alkoxymethylene-2,4-dicarbonyl derivative (III) with a formamidine.

(2) Synthesis route (2) in Scheme 1 indicates a method of producing apyrimidine derivative (V) of the present invention (wherein X: C═O),which comprises reacting a 2,4-dicarbonyl compound (II) with anN,N-dimethylformamide dialkylacetal ortert-butoxy-bis(dimethylamino)methane and then reacting the resulting3-dimethylaminomethylene-2,4-dicarbonyl derivative (IV) with aformamidine. ##STR4##

(3) Scheme 2 indicates a method wherein a pyrimidine derivative (V)(wherein X: C═O) is converted into a corresponding alcohol (VI) (X:CH--OH) by a suitable reduction method (for example, NaBH₄ or BH₃) orasymmetric reduction.

When the resulting alcohol (VI) is racemic, each of the optically activealcohols can be obtained through a suitable optical resolution, ifnecessary. ##STR5##

(4) Scheme 3 indicates a method of producing a compound (VII), whichcomprises reacting a pyrimidine derivative (V) with R3-Met-Hal (providedthat the case that R3 is a hydrogen atom is excluded).

Now, the syntheses of the compounds of the present invention and theirintermediates will be described in detail with reference to Examples.However, it should be understood that the present invention is by nomeans restricted by such specific Examples.

BEST MODE OF AN EMBODIMENT OF THE PRESENT INVENTION EXAMPLE 1 Synthesisof 1-Choro-1,1-difluoro-3-ethoxymethylene-2,4-pentanedione (Compound No.203) ##STR6##

A mixed solution containing 50 g of1-chloro-1,1-difluoro-2,4-pentanedione, 60 g of ethyl orthoformate and82 g of acetic anhydride was refluxed with stirring for 2 hours. After aDean-Stark apparatus (water separator) was fixed, the solution wasrefluxed for additional 4 hours, while about 100 ml of water wasremoved. After it was allowed to cool, vacuum distillation was conductedto obtain 32.2 g of the desired product as a pale red liquid. Boilingpoint 95°-118° C./1.6 mmHg.

EXAMPLE 2 Synthesis of 5-Acetyl-4-chlorodifluoromethylpyrimidine(Compound No. 1) ##STR7##

To 50 ml of dry ethanol, 0.9 g of metal sodium was added under coolingwith ice to prepare sodium ethoxide. To this solution, 8.4 g offormamidine acetate which had been fully dried by means of a vacuum pumpwas added with stirring. Then, a solution of 8 g of1-chloro-1,1-difluoro-3-ethoxymethylene-2,4-pentanedione dissolved in 20ml of ethanol was added dropwise under cooling with ice. After thedropwise addition, the reaction solution was warmed to room temperature,and heated and refluxed with heating for 1.5 hours. The reactionsolution was allowed to cool and after addition of water, etherextraction was carried out. The ether layer was dried over anhydroussodium sulfate, and the solvent was distilled off under reducedpressure. The residue was subjected to vacuum distillation, and afterpurification by column chromatography (developing solvent: CHCl₃), 2.5 gof the desired product was obtained. Boiling point 65°-70° C./1.3 mmHg,n_(D) ²⁰.7 1.4787

EXAMPLE 3 Synthesis of4-Chlorodifluoromethyl-5-(1-hydroxyethyl)pyrimidine (Compound No. 101)##STR8##

0.4 g of 5-acetyl-4-chlorodifluoromethylpyrimidine was dissolved in 10ml of dry diethyl ether, then, an excess of a borane ammonia complex wasadded under cooling with ice, and the mixture was stirred overnight atroom temperature. After addition of water, extraction with diethyl etherwas carried out. The ether layer was dried over anhydrous sodiumsulfate, and the solvent was distilled off under reduced pressure toobtain 0.32 g of the desired product as a viscous liquid. n_(D) ¹⁹.91.4899

EXAMPLE 4 Synthesis of 5-(1-Hydroxyethyl)-4-trifluoromethylpyrimidine(Compound No. 102) ##STR9##

0.5 g of 5-acetyl-4-trifluoromethylpyrimidine was dissolved in 10 ml ofdry methanol. 0.03 g of sodium boron hydride was added, and the mixturewas stirred for 30 minutes under cooling with ice, and then furtherstirred overnight at room temperature. After the completion of thereaction, the solvent was distilled off, and 40 ml of a 1:1 solventmixture of chloroform/water was added for chloroform extraction. Afterthe chloroform layer was dried over anhydrous sodium sulfate, thesolvent was distilled off under reduced pressure. After purification bycolumn chromatography, 0.2 g of the desired product was obtained as aviscous liquid. n_(D) ¹⁹.9 1.4549

EXAMPLE 5 Synthesis of1-Chloro-1,1-difluoro-5,5-dimethyl-2,4-hexanedione (Compound No. 301)##STR10##

7.1 g of sodium methoxide was added to 100 ml of dry ether, and themixture was stirred. A solution of 20 g of ethyl chlorodifluoroacetatediluted with 25 ml of dry ether was added dropwise at room temperature.Further, a solution of 12.5 g of pinacolone diluted with 25 ml of dryether was added dropwise, and the mixture was stirred overnight at roomtemperature. Then, to the reaction solution, a solution of 8.4 g ofglacial acetic acid diluted with 100 ml of water and a solution of 23.6g of copper (II) acetate dissolved in a proper amount of water wereadded dropwise successively. The dropwise addition was followed bystirring for about 10 minutes. Then, the ether was distilled off underreduced pressure and the solid mass was filtered off. After vacuumdrying, 100 ml of 6N hydrochloric acid was added, and extraction withethyl acetate was carried out. The ethyl acetate layer was dried overanhydrous sodium sulfate, and the solvent was distilled off underreduced pressure. Then, the residue was subjected to vacuum distillationto obtain 13 g of the desired product. (b.p. 54°-57° C./5 mmHg)

¹ H-NMR δ(ppm) solvent!; 1.24 (s, 9H, C(CH₃)₃) 5.95 (s, 1H, enol olefin)14.00 (br s, 1H, enol OH), CDCl₃ !, ¹³ C-NMR δ(ppm) solvent!; 27.2 (s,C(CH₃)₃) 39.3 (s, C(CH₃)₃) 90.0 (t, J_(F),C =2 Hz, ClCF₂ C═C) 120.3 (t,J_(F),C =299 Hz, CF₂ Cl) 180.3 (t, J_(F),C =30 Hz, ClCF₂ C═C) 202.2 (s,COC(CH₃)₃) CDCl₃ !, ¹⁹ F-NMR δ(ppm) solvent!; 13.3 (s, 2F, ClCF₂) (ref.CF₃ CO₂ H) CDCl₃ !.

EXAMPLE 6 Synthesis of1-Chloro-1,1-difluoro-5,5-dimethyl-3-ethoxymethylene-2,4-hexanedione(Compound No. 204) ##STR11##

12.4 g of 1-chloro-1,1-difluoro-5,5-dimethyl-2,4-hexanedione and 12.4 gof ethyl orthoformate were added to 50 ml of acetic anhydride, and themixture was refluxed under heating for 2 hours. After the solvent wasdistilled off under reduced pressure, the residue was subjected tovacuum distillation to obtain 6.8 g of the desired product. (b.p.105°-107° C./2 mmHg)

EXAMPLE 7 Synthesis of 4-Chlorodifluoromethyl-5-pivaloylpyrimidine(Compound No. 3) ##STR12##

0.7 g of sodium methoxide and 1.25 g of formamidine acetate were addedto 30 ml of dry methanol, and the mixture was stirred at roomtemperature for 30 minutes. A solution of 3 g of1-chloro-1,1-difluoro-5,5-dimethyl-3-ethoxymethylene-2,4-hexanedionediluted with 5 ml of dry methanol was added dropwise, and after theaddition, the mixture was refluxed under heating for 2 hours. Thesolvent was distilled off under reduced pressure, and after addition ofwater, extraction with ethyl acetate was carried out. The ethyl acetatelayer was dried over anhydrous sodium sulfate, and the solvent wasdistilled off under reduced pressure. The residue was purified bythin-layer chromatography (developing solvent: hexane 80%, ethyl acetate20%) to obtain 0.6 g of the desired product. n_(D) ²⁰.0 1.4675

EXAMPLE 8 Synthesis of4-Chlorodifluoromethyl-5-(2,2-dimethyl-1-hydroxypropyl)pyrimidine(Compound No. 103) ##STR13##

1.5 g of 4-chlorodifluoromethyl-5-pivaloylpyrimidine was dissolved in 50ml of ethanol, then 1 g of a boron ammonia complex was added, and themixture was stirred at room temperature for 1 hour. After the solventwas distilled off under reduced pressure, water was added, andextraction with chloroform was carried out. The extract layer was washedwith water and then dried over anhydrous sodium sulfate. The solvent wasdistilled off under reduced pressure, and the residue was purified bythin-layer chromatography (developing solvent: chloroform/ethylacetate=7/3) to obtain 1.1 g of the desired product as a viscous liquid.n_(D) ¹⁹.8 1.4623

EXAMPLE 9 Synthesis of 1-(4-Chlorophenyl)-4,4-dimethylpentane-1,3-dione(Compound No. 303) ##STR14##

30 g of methyl 4-chlorobenzoate was dissolved in anhydrous THF, and 16.9g of 60% sodium hydride was added under cooling with ice. 21.1 g ofpinacolone was added dropwise, and the mixture was stirred under heatingat 50° C. for 6 hours. Then, 100 ml of water was added dropwise undercooling with ice, and the solvent was distilled off under reducedpressure. 200 ml of water and 100 ml of 6N hydrochloric acid were addedthereto, and then extraction with ethyl acetate was carried out. Theextract layer was dried over anhydrous sodium sulfate, and the solventwas distilled off under reduced pressure. The residue was purified bysilica gel column chromatography (developing solvent:chloroform/hexane=2/8) to obtain 43 g of the desired product as aviscous liquid. n_(D) ²⁰.0 1.5012

EXAMPLE 10 Synthesis of1-(4-Chlorophenyl)-4,4-dimethyl-2-(N,N-dimethylaminomethylene)-1,3-pentanedione(Compound No. 206) ##STR15##

17 g of 1-(4-chlorophenyl)-4,4-dimethyl-1,3-pentanedione and 18 g ofdimethylformamide dimethylacetal were added to 200 ml of dry toluene,and the mixture was refluxed under heating for 2 hours, and then themethanol was distilled off over 1 hour. The solvent was distilled off,and the residue was purified by silica gel chromatography (developingsolvent: chloroform/hexane=6/4) to obtain 13.7 g of the desired productas a pale yellow solid.

m.p. 102°-104° C.

EXAMPLE 11 Syntheses of 4-(4-Chlorophenyl)-5-pivaloylpyrimidine and4-t-Butyl-5-(4-chlorobenzoyl)pyrimidine (Compounds Nos. 5 and 6)##STR16##

1 g of metal sodium and 3.3 g of formamidine acetate were added to 150ml of absolute ethanol, and the mixture was stirred at room temperaturefor 15 minutes. 8.5 of1-(4-chlorophenyl)-4,4-diemthyl-2-(N,N-dimethylaminomethylene)-1,3-pentanedionewas added thereto, and the mixture was refluxed under heating for 3hours. 20 cc of water was added at room temperature, and then thesolvent was distilled off under reduced pressure. After further additionof water, extraction with ethyl acetate was conducted. The extract layerwas washed with water and dried over anhydrous sodium sulfate. Thesolvent was distilled off under reduced pressure, and the residue wasseparated by silica gel column chromatography (developing solvent; ethylacetate/hexane=3/7) to obtain 4-t-butyl-5-(4-chlorobenzoyl)pyrimidine(yield: 2.5g, m.p.:75°-77° C.) and4-(4-chlorophenyl)-5-pivaloylpyrimidine (yield 2.4 g, n_(D) ²⁰.11.5784).

EXAMPLE 12 Synthesis of4-(4-Chlorophenyl)-5-(2,2-dimethyl-1-hydroxypropyl)pyrimidine (CompoundNo. 104) ##STR17##

1.2 g of 4-(4-chlorophenyl)-5-pivaloylpyrimidine was dissolved in 20 mlof ethanol, then 1.2 g of a borane ammonia complex was added, and themixture was stirred at room temperature for 30 minutes. After thesolvent was distilled off under reduced pressure, water was added, andextraction with chloroform was carried out. The extract layer was washedwith water and dried over anhydrous sodium sulfate. The solvent wasdistilled off to obtain 0.8 g of the desired product as a viscousliquid. n_(D) ²⁰.2 1.5575

EXAMPLE 13 Synthesis of 4-t-Butyl-5-(4-chlorophenyl)hydroxymethyl!pyrimidine (Compound No. 105) ##STR18##

1 g of 4-t-butyl-5-(4-chlorobenzoyl)pyrimidine was dissolved in 20 ml ofethanol, and 0.8 g of a borane ammonia complex was added. The mixturewas heated at 50° C.-60° C. for 1 hour, and further refluxed underheating for 30 minutes. After the solvent was distilled off underreduced pressure, water was added, and extraction with chloroform wascarried out. The extract layer was washed with water and dried overanhydrous sodium sulfate. The solvent was distilled off under reducedpressure to obtain 0.6 g of the desired product as a viscous liquid.n_(D) ²⁰.2 1.5474

EXAMPLE 14 Synthesis of1-Chloro-4-(4-chlorophenyl)-1,1-difluoro-2,4-butanedione (Compound No.318) ##STR19##

38 g of ethyl chlorodifluoroacetate was added to 22.7 g of sodiummethoxide and 300 ml of dry ether under cooling with ice. 31 g ofp-chloroacetophenone was gradually added thereto under cooling with ice.The mixture was stirred at room temperature for 12 hours. The solventwas distilled off. 150 ml of 6N hydrochloric acid was added undercooling with ice, and extraction with ethyl acetate was carried out. Theextract layer was washed with water, and the solvent was distilled off.The resulting crude product was purified by silica gel columnchromatography (developing solvent: chloroform), and thereby 49.5 g ofthe desired product was obtained as a pale yellow viscous liquid. m.p.50°-51° C.

EXAMPLE 15 Synthesis of1-Chloro-4-(4-chlorophenyl)-1,1-difluoro-3-ethoxymethylene-2,4-butanedione##STR20##

A mixture of 49.5 g of1-choro-4-(4-chlorophenyl)-1,1-difluoro-2,4-butanedione, 41.3 g of ethylorthoformate and 57 g of acetic anhydride was refluxed under heating for4 days. The solvent was distilled off to obtain 60.4 g of the crudeproduct, which was used for the next reaction directly.

EXAMPLE 16 Synthesis of5-(4-Chlorobenzoyl)-4-chlordifluoromethylpyrimidine (Compound No. 20)##STR21##

6 g of metal sodium and 500 ml of dry ethanol was mixed to prepare asodium ethoxide solution. 23.3 g of formamidine acetate was added to thesolution, and the mixture was stirred at room temperature for 15minutes. 60.4 g of1-chloro-4-(4-chlorophenyl)-1,1-difluoro-3-ethoxymethylene-2,4-butanedione(crude product) was gradually added under cooling with ice. The mixturewas refluxed under heating for 2 hours. The solvent was distilled offunder reduced pressure. 300 ml of ice water was added, and thenextraction with ethyl acetate was carried out. The extract layer waswashed with water, and the solvent was distilled off under reducedpressure.

The resulting crude product was purified by silica gel columnchromatography (developing solvent: chloroform/hexane=1/1) to obtain 27g of the desired product as a pale yellow liquid. n_(D) ²⁰.8 1.5742

EXAMPLE 17 Synthesis of 4-Chlorodifluoromethyl-5-(4-chlorophenyl)hydroxymethyl!pyrimidine (Compound No. 119) ##STR22##

12 g of 5-(4-chlorobenzoyl)-4-chlorodifluoromethylpyrimidine and 6 g ofa t-butylamine borane complex were added to 100 ml of ethanol, and theresulting mixture was stirred at 0° C. for 2 hours. Then, 20 ml ofacetone was added thereto, and the mixture was stirred at 0° C. for 1hour. The solvent was distilled off under reduced pressure, and theresidue was purified by silica gel column chromatography (developingsolvent: chloroform) to obtain 11.1 g of the desired product as a paleyellow viscous liquid. n_(D) ²⁰.3 1.5563

EXAMPLE 18 Synthesis of1-Chloro-4-cyclohexyl-1,1-difluoro-2,4-butanedione (Compound No. 305)##STR23##

74.8 g of sodium methoxide was added to 1 l of ether, and a solution of200 g of ethyl chlorodifluoroacetate in 300 ml of ether was addeddropwise thereto under stirring at 0° C. Then, a solution of 106 g ofcyclopropyl methyl ketone in 300 ml of ether was gradually added to thereaction solution, and after the addition, the mixture was stirred atroom temperature for 8 hours. The solvent was distilled off underreduced pressure, 300 ml of 6N hydrochloric acid was added to theresidue, and extraction with ethyl acetate was carried out. The extractlayer was washed with water, and the solvent was distilled off underreduced pressure to obtain 235.9 g of the desired product as a paleyellow liquid. n_(D) ²⁰.6 1.4788

EXAMPLE 19 Synthesis of1-Chloro-4-cyclohexyl-3-ethoxymethylene-1,1-difluoro-2,4-butanedione(Compound No. 207) ##STR24##

A mixture of 235.9 g of1-chloro-4-cyclohexyl-1,1-difluoro-2,4-butanedione, 266.4 g of ethylorthoformate and 367.2 g of acetic anhydride was refluxed under heatingfor 12 hours. The solvent was distilled off under reduced pressure toobtain 280.3 g of the desired product (crude product), which wasdirectly used for the next reaction. A part of the crude product wasfurther purified for measurement of the refractive index. n_(D) ²⁰.61.4787

EXAMPLE 20 Synthesis of4-Chlorodifluoromethyl-5-cyclopropylcarbonylpyrimidine (Compound No. 7)##STR25##

71.9 of sodium methoxide was added to 1 l of ethanol, and then 121.2 gof formamidine acetate was added. To the resulting mixture, 280 g of1-chloro-4-cyclohexyl-3-ethoxymethylene-1,1-difluoro-2,4-butanedione wasgradually added dropwise under cooling with ice. The mixture wasrefluxed under heating for an hour, and the solvent was distilled offunder reduced pressure. 500 ml of water was added to the residue, andextraction with ethyl acetate was carried out. The solvent in theextract layer was distilled off under reduced pressure, and the residuewas purified by silica gel column chromatography (developing solvent:chloroform/hexane=1/1) to obtain 101 g of the desired product. n_(D)²⁰.5 1.4998

EXAMPLE 21 Synthesis of4-Chlorodifluoromethyl-5-(1-hydroxycyclopropylmethyl)pyrimidine(Compound No. 106) ##STR26##

70 g of 4-chlorodifluoromethyl-5-cyclopropylcarbonylpyrimidine was addedto 100 ml of ethanol, then, 15 g of a t-butylamine borane complex wasfurther added under cooling with ice, and the mixture was stirred atroom temperature for 2 hours. After addition of 30 ml of acetone, themixture was stirred at room temperature for 1 hour, and the solvent wasdistilled off under reduced pressure. 100 ml of water was added to theresidue, and extraction with ethyl acetate was carried out. The extractlayer was washed with water, and the solvent was distilled off underreduced pressure. The residue was dried in vacuum to obtain 45 g of thedesired product. n_(D) ²⁰.5 1.5020

EXAMPLE 22 Synthesis of 4-Chlorodifluoromethyl-5-bromoacetylpyrimidine(Compound No. 11) ##STR27##

A mixture of 2.0 g of 5-acetyl-4-chlorodifluoromethylpyrimidine, 4.3 gof cupric bromide (CuBr₂) and 20 ml of dry dioxane was stirred at roomtemperature for a day, and then stirred under reflux for another day.Then, the insolubles were filtrated off and washed with a small amountof chloroform, and the filtrate thus obtained was distilled underreduced pressure. The resulting crude product was purified bypreparative thin-layer chromatography (developing solvent: chloroform)to obtain 640 mg of the desired product as a pale yellow liquid.

EXAMPLE 23 Synthesis of4-Chlorodifluoromethyl-5-(1-hydroxy-1-methylethyl)pyrimidine (CompoundNo. 110) ##STR28##

To a mixture of 470 mg of magnesium and 5 ml of dry ethyl ether, asolution of 2.76 g of methyl iodide dissolved in 15 ml of dry ethylether was added dropwise while the reaction mixture was kept undercontrol so as to be refluxed moderately. After the dropwise addition, itwas further refluxed for 45 minutes. The reaction mixture was allowed tocool to room temperature, then, 2 g of5-acetyl-4-chlorodifluoromethylpyrimidine was quickly added dropwisethereto, and the reaction mixture was refluxed for another 1 hour. Thereaction mixture was cooled with ice, and stirred while a saturatedaqueous solution of ammonium chloride was added thereto. The ether layerwas separated by decantation and washed with saturated aqueous saltsolution three times in a separatory funnel. The organic layer was driedover anhydrous sodium sulfate, and the solvent was distilled off. Theresulting crude product was subjected to preparatory thin-layerchromatography (developing solvent: chloroform) three times, and as aresult, 131 mg of the desired product was obtained as a viscous liquid.n_(D) ²⁰.6 1.4982

EXAMPLE 24 Synthesis of 4-tert-Butyl-5-(2-methylphenyl)hydroxymethyl!pyrimidine (Compound No. 117) ##STR29##

500 ml of sodium boron hydride (purity 92%) was added to a mixture of 1g of 4-tert-butyl-5-(2-methylbenzoyl)pyrimidine and 20 ml of drymethanol, under cooling with ice, and the resulting mixture was stirredfor 2 hours. The solvent was distilled off under reduced pressure, andto the resulting mixture, ice water and ethyl acetate were added, andthe pH was adjusted to a level from 1 to 2 with concentratedhydrochloric acid with stirring. The organic layer was washed withsaturated aqueous salt solution twice, and then dried over anhydroussodium sulfate. The solvent was distilled off under reduced pressure toobtain 600 mg of the desired product as white crystals.

m.p. 125°-127° C.

The structures, the spectral data and the physical properties of thecompounds of the present invention synthesized in the same manner as theabove examples, including the compounds synthesized in the precedingExamples, are shown Tables 1-1, 1-2, 2-1 and 2-2. The structures and thephysical properties of their intermediates are shown Tables 3-1 and 3-2.

                  TABLE 1-1                                                       ______________________________________                                         ##STR30##                                                                    Comp. No.    R1            R2                                                 ______________________________________                                         1           CF.sub.2 Cl   Me                                                  2           CF.sub.3      Me                                                  3           CF.sub.2 Cl   Bu.sup.tert                                         4           CF.sub.2 CF.sub.3                                                                           Me                                                  5           4-Cl-Phenyl   Bu.sup.tert                                         6           Bu.sup.tert   4-Cl-Phenyl                                         7           CF.sub.2 Cl   Pr.sup.cyclo                                        8           2,4-Cl.sub.2 -Phenyl                                                                        Bu.sup.tert                                         9           Bu.sup.tert   2,4-Cl.sub.2 -Phenyl                               10           CF.sub.2 Cl   Et                                                 11           CF.sub.2 Cl   CH.sub.2 Br                                        12           4-Cl-Phenyl   Pr.sup.cyclo                                       13           CF.sub.2 Cl   Pr.sup.n                                           14           CF.sub.2 Cl   Pr.sup.iso                                         15           Bu.sup.tert   4-MeO-Phenyl                                       16           Bu.sup.tert   2-MeO-Phenyl                                       17           CF.sub.2 CF.sub.2 Cl                                                                        Me                                                 18           Bu.sup.tert   3-Me-Phenyl                                        19           Bu.sup.tert   2-Me-Phenyl                                        20           CF.sub.2 Cl   4-Cl-Phenyl                                        21           CF.sub.2 Cl   2,4-Cl.sub.2 -Phenyl                               22           CF.sub.2 Br   Me                                                 23           CF.sub.2 Cl   Phenyl                                             24           CF.sub.2 Cl   4-F-Phenyl                                         25           CF.sub.2 Cl   2-F-Phenyl                                         26           CF.sub.2 Cl   3-F-Phenyl                                         27           CF.sub.2 Cl   2-Cl-Phenyl                                        28           CF.sub.2 Cl   3-Cl-Phenyl                                        29           CF.sub.2 Cl   3,4-Cl.sub.2 -Phenyl                               30           CHFCl         Pr.sup.n                                           31           CF.sub.2 H    Pr.sup.n                                           32           CF.sub.2 Cl   2-Me-Phenyl                                        ______________________________________                                    

                  TABLE 1-2                                                       ______________________________________                                        Comp.                         Physical                                        No.   Spectral data           Properties                                      ______________________________________                                         1    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.7 1.4787,                              2.65(t, J=1Hz, 3H, COCH.sub.3),                                                                       bp 65-70° C./                                  8.90(s, 1H),            1.3 mmHg                                              9.42(s, 1H),                                                                   CDCl.sub.3)                                                                  .sup.13 C-NMR δ (ppm)  solvent!;                                        31.35 (t,J.sub.F,C =2.7Hz, COCH.sub.3)                                        122.99(t, J.sub.F,C =291Hz, CF.sub.2 Cl),                                     131.26(s, pyrimidine ring, 5-position),                                       155.07(t, J.sub.F,C =31Hz, pyrimiding ring,                                   4-position),                                                                  156.91(s, pyrimidine ring, 6-position),                                       159.20(s, pyrimidine ring, 2-position),                                       197.69(s, C═O),                                                            CDCl.sub.3 !                                                                 .sup.19 F-NMR δ (ppm)  solvent!;                                        24.0(s, 2F, ClCF.sub.2),                                                      (ref. CF.sub.3 CO.sub.2 H),                                                    CDCl.sub.3 !                                                            2    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 bp 65-66° C.                                   2.68(s, 3H, COCH.sub.3),                                                                              3.5 mmHg                                              9.07(s, 1H),                                                                  9.48(s, 1H),                                                                   CDCl.sub.3 !                                                                 .sup.13 C-NMR δ (ppm)  solvent!;                                        30.85(s, COCH.sub.3),                                                         120.34(q, J.sub.F,C =276Hz, CF.sub.3),                                        132.63(s, pyrimidine ring, 5-position),                                       151.26(q, J.sub.F,C =37Hz, pyrimidine ring,                                   4-position),                                                                  157.14(s, pyrimidine ring),                                                   159.42(s, pyrimidine ring),                                                   197.19(s, C═O),                                                            CDCl.sub.3 !                                                            3    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.0 1.4675                               1.28(s, 9H, C(CH.sub.3).sub.3),                                               8.75(s, 1H, pyrimidine),                                                      9.34(s, 1H, pyrimidine),                                                       CDCl.sub.3 !                                                                 .sup.13 C-NMR δ (ppm)  solvent!:                                        26.8(s, C(CH.sub.3).sub.3),                                                   45.2(s, C(CH.sub.3).sub.3),                                                   123.0(t, J.sub.F,C =291Hz, ClCF.sub.2),                                       130.1(s, pyrimidine ring, 5-position),                                        154.9(t, J.sub.F,C =31Hz, pyrimidine ring,                                    4-position),                                                                  155.2(s, pyrimidine ring),                                                    158.3(s, pyrimidine ring),                                                    207.2(s, C═O),                                                             CDCl.sub.3 !                                                                 .sup.19 F-NMR δ (ppm)  solvent!:                                        23.8(s, 2F, ClCF.sub.2),                                                      (ref. CF.sub.3 CO.sub.2 H),                                                    CDCl.sub.3 !                                                            4    .sup.1 H-NMR δ (ppm)  solvent!:                                                                 n.sub.D.sup.20.1 1.4335                               2.60(t, J=1Hz, 3H, COCH.sub.3),                                               8.85(s, 1H, Pyrimidine ring),                                                 9.37(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3 !                                                            5    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.1 1.5784                               0.97(s, 9H, C(CH.sub.3).sub.3),                                               7.46(d, J=9Hz, 2H, Benzene ring),                                             7.65(d, J=9Hz, 2H, Benzene ring),                                             8.56(s, 1H, Pyrimidine ring),                                                 9.30(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3 !                                                                 .sup.13 C-NMR δ (ppm)  solvent!;                                        26.7(s, C(CH.sub.3).sub.3),                                                   45.9(s, C(CH.sub.3).sub.3),                                                   129.3(s, Benzene ring CH),                                                    130.6(s, Benzene ring CH),                                                    133.2(s, Pyrimidine ring, 5-position),                                        136.6(s, Benzene ring),                                                       137.2(s, Benzene ring),                                                       154.6(s, Pyrimidine ring, 6-position, CH),                                    158.4(s, Pyrimidine ring, 2-position, CH),                                    160.1(s, Pyrimidine ring, 4-Position),                                        212.1(s, COC(CH.sub.3).sub.3),                                                 CDCl.sub.3 !                                                            6    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 bp 75˜77° C.                             1.33(s, 9H, C(CH.sub.3).sub.3),                                               7.49(d, J=9Hz, 2H, Benzene ring),                                             7.77(d, J=9Hz, 2H, Benzene ring),                                             8.42(s, 1H, Pyrimidine ring)                                                  9.24(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                                 .sup.13 C-NMR δ (ppm)  solvent!;                                        30.0(s, C(CH.sub.3).sub.3);                                                   39.9(s, C(CH.sub.3).sub.3);                                                   129.4(s, Benzene ring CH),                                                    131.5(s, Benzene ring CH),                                                    131.5(s, Pyrimidine ring, 5-position)                                         135.4(s, Benzene ring),                                                       141.1(s, Benzene ring),                                                       155.2(s, Pyrimidine ring, 6-position)                                         158.1(s, Pyrimidine ring, 2-position, CH),                                    174.4(s, Pyrimidine ring, 4-position, CH),                                    194.7(s, CO),                                                                  CDCl.sub.3 !                                                            7    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.5 1.4998                               1.11-1.47(m, 4H, cyclopropane ring                                            (methylene))                                                                  2.10-2.50(m, 1H, cyclopropane ring(methine))                                  8.85(s, 1H, pyrimidine ring)                                                  9.32(s, 1H, pyrimidine ring)                                                   CDCl.sub.3 !                                                            8    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.1 1.5571                               1.06(s, 9H, C(CH.sub.3).sub.3                                                 6.89˜7.37(m, 3H, Benzene ring)                                          8.67(s, 1H, Pyrimidine ring)                                                  9.19(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                            9    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 102-                                               1.35(s, 9H, C(CH.sub.3).sub.3)                                                                        103° C.                                        6.83˜7.08(m, 2H, Benzene ring)                                          7.70˜7.75(m, 1H, Benzene ring)                                          8.17(s, 1H, Pyrimidine ring)                                                  9.01(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           10    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.4 1.4745                               1.23(t, J=7Hz, 3H, CH.sub.2 CH.sub.3)                                         2.88(q, J=7Hz, 2H, CH.sub.2 CH.sub.3)                                         8.77(s, 1H, Pyrimidine ring)                                                  9.32(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           11    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 oil                                                   4.30(s, 2H, CH.sub.2 Br)                                                      8.90(s, 1H, Pyrimidine ring)                                                  9.38(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 9                                                           12    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp. 110-                                              0.72˜1.40(m, 4H, cyclo-propyl CH.sub.2)                                                         112° C.                                        1.59˜2.01(m, 1H, cyclo-propyl CH)                                       7.40(d, J=9Hz, 2H, Benzene ring)                                              7.62(d, J=9Hz, 2H, Benzene ring)                                              8.77(s, 1H, Pyrimidine ring)                                                  9.22(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           13    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.7 1.4770                               1.00(t, J=7Hz, 3H, CH.sub.2 CH.sub.2 CH.sub.3)                                1.74(tq, J=7, 7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3)                            2.82(t, J=7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3)                                8.77(s, 1H, Pyrimidine ring)                                                  9.33(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           14    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.5 1.4732                               0.97˜1.46(m, 4H, cyclo-propyl CH.sub.2)                                 2.00˜2.42(m, 1H, cyclo-propyl CH)                                       8.84(s, 1H, Pyrimidine ring)                                                  9.29(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           15    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 91-93° C.                                   1.16(s, 9H, C(CH.sub.3).sub.3)                                                3.91(s, 3H, OCH.sub.3)                                                        7.00(d, J=9Hz, 2H, Benzene ring)                                              7.83(d, J=9Hz, 2H, Benzene ring)                                              8.47(s, 1H, Pyrimidine ring)                                                  9.27(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           16    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 71-73° C.                                   1.38(s, 9H, C(CH.sub.3).sub.3)                                                3.60(s, 3H, OCH.sub.3)                                                        6.90˜8.10(m, 4H, Benzene ring)                                          8.37(s, 1H, Pyrimidine ring)                                                  9.19(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           17    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.2 1.4519                               2.61(t, J=1Hz, 3H, CH.sub.3)                                                  8.85(s, 1H, Pyrimidine ring)                                                  9.41(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           18    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 98-100° C.                                  1.34(s, 9H, C(CH.sub.3).sub.3)                                                2.42(s, 3H, CH.sub.3)                                                         7.30˜7.80(m, 4H, Benzene ring)                                          8.46(s, 1H, Pyrimidine ring)                                                  9.27(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           19    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 57-59° C.                                   1.36(s, 9H, C(CH.sub.3).sub.3)                                                2.73(s, 3H, CH.sub.3)                                                         6.80-7.80(m, 4H, Benzene ring)                                                8.45(s, 1H, Pyrimidine ring)                                                  9.25(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           20    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.3 1.5742                               7.51(d, J=9Hz, 2H, Benzene ring)                                              7.72(d, J=9Hz, 2H, Benzene ring)                                              8.88(s, 1H, Pyrimidine ring)                                                  9.50(s, 1H, Pyrimidine ring)                                            21    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.5 1.5837                               7.19˜7.69(m, 3H, Benzene ring)                                          8.78(s, 1H, Pyrimidine ring)                                                  9.36(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           22    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.9 1.5069                               2.62(s, 3H, CH.sub.3)                                                         8.79(s, 1H, Pyrimidine ring)                                                  9.32(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           23    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.1 1.5571                               7.34˜7.84(m, 5H, Benzene ring)                                          8.76(s, 1H, Pyrimidine ring)                                                  8.87(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           24    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 63-64° C.                                   6.95˜8.00(m, 4H, Benzene ring)                                          8.82(s, 1H, Pyrimidine ring)                                                  9.43(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           25    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.8 1.5468                               6.85-8.10(m, 4H, Benzene ring)                                                8.75(s, 1H, Pyrimidine ring)                                                  9.34(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           26    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 40-42° C.                                   7.10-7.82(m, 4H, Benzene ring)                                                8.75(s, 1H, Pyrimidine ring)                                                  9.46(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           27    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.8 1.5612                               7.17-7.76(m, 4H, Benzene ring)                                                8.77(s, 1H, Pyrimidine ring)                                                  9.35(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           28    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.8 1.5756                               7.34-7.76(m, 4H, Benzene ring)                                                8.79(s, 1H, Pyrimidine ring)                                                  9.39(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           29    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 mp 51-53° C.                                   7.37-7.91(m, 3H, Benzene ring)                                                9.00(s, 1H, Pyrimidine ring)                                                  9.63(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           30    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.0 1.5113                               1.01(t, J=7Hz, 3H, CH.sub.2 CH.sub.2 CH.sub.3)                                1.77(tq, J=7.7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3)                             2.96(t, J=7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3)                                7.58(d, J=50Hz, 1H, CHFCl)                                                    9.05(s, 1H, Pyrimidine ring)                                                  9.30(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           31    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.19.8 1.4830                               1.00(t, J=7Hz, 3H, CH.sub.2 CH.sub.2 CH.sub.3)                                1.77(tq, J=7.7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3)                             2.95(t, J=7Hz, 2H, CH.sub.2 CH.sub.2 CH.sub.3))                               6.88(t, J=53Hz, 1H, CHF.sub.2)                                                9.01(s, 1H, Pyrimidine ring)                                                  9.30(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           32    .sup.1 H-NMR δ (ppm)  solvent!;                                                                 n.sub.D.sup.20.4 1.5588                               2.67(s, 3H, CH.sub.3)                                                         7.10-7.45(m, 4H, Benzene ring)                                                8.88(s, 1H, Pyrimidine ring)                                                  9.46(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           ______________________________________                                    

                  TABLE 2-1                                                       ______________________________________                                         ##STR31##                                                                    Comp. No.  R1           R2           R3                                       ______________________________________                                        101        CF.sub.2 Cl  Me           H                                        102        CF.sub.3     Me           H                                        103        CF.sub.2 Cl  Bu.sup.tert  H                                        104        4-Cl-Phenyl  Bu.sup.tert  H                                        105        Bu.sup.tert  4-Cl-Phenyl  H                                        106        CF.sub.2 Cl  Pr.sup.cyclo H                                        107        CF.sub.2 CF.sub.3                                                                          Me           H                                        108        2,4-Cl.sub.2 -Phenyl                                                                       Bu.sup.tert  H                                        109        Bu.sup.tert  2,4-Cl.sub.2 -Phenyl                                                                       H                                        110        CF.sub.2 Cl  Me           Me                                       111        CF.sub.2 Cl  Pr.sup.n     H                                        112        CF.sub.2 Cl  Et           H                                        113        4-Cl-Phenyl  Pr.sup.cyclo H                                        114        CF.sub.2 Cl  Pr.sup.iso   H                                        115        Bu.sup.tert  4-MeO-Phenyl H                                        116        Bu.sup.tert  2-MeO-Phenyl H                                        117        Bu.sup.tert  2-Me-Phenyl  H                                        118        Bu.sup.tert  3-Me-Phenyl  H                                        119        CF.sub.2 Cl  4-Cl-Phenyl  H                                        120        CF.sub.2 CF.sub.2 Cl                                                                       Me           H                                        121        CF.sub.2 Cl  2,4-Cl.sub.2 -Phenyl                                                                       H                                        122        CF.sub.2 Br  Me           H                                        123        CF.sub.2 Cl  Phenyl       H                                        124        CF.sub.2 Cl  4-F-Phenyl   H                                        125        CF.sub.2 Cl  2-F-Phenyl   H                                        126        CF.sub.2 Cl  2-Cl-Phenyl  H                                        127        CF.sub.2 Cl  3-Cl-Phenyl  H                                        128        CF.sub.2 Cl  3,4-Cl.sub.2 -Phenyl                                                                       H                                        129        CF.sub.2 Cl  3-F-Phenyl   H                                        ______________________________________                                    

                  TABLE 2-2                                                       ______________________________________                                        Comp.                        Physical                                         No.   Spectral data          properties                                       ______________________________________                                        101   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.9 1.4899                                1.55(d, J=6Hz, 3H, CH.sub.3),                                                 2.72(br s, 1H, OH),                                                           5.42(qd, J=6, 2Hz, 1H, CH),                                                   9.10(s, 1H),                                                                  9.20(s, 1H),                                                                   CDCl.sub.3 !                                                           102   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.9 1.4549                                1.55(d, J=6Hz, 3H, CH.sub.3),                                                 2.95(d, J=3Hz, 1H, OH),                                                       5.1˜5.6(br m, 1H, CH),                                                  9.20(s, 1H),                                                                  9.27(s, 1H),                                                                   CDCl.sub.3 !                                                           103   MS(FAB+) m/z: 251  M+H!.sup.+,                                                                       n.sub.D.sup.19.8 1.4623                                .sup.1 H-NMR δ (ppm)  solvent!;                                         0.93˜0.99(m, 9H, C(CH.sub.3).sub.3),                                    3.03˜3.85(br m, 1H, OH)                                                 5.08(s, 1H, CHOH),                                                            9.21(s, 1H, Pyrimidine ring),                                                 9.25(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3 !                                                           104   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.2 1.5575                                0.71(s, 9H, C(CH.sub.3).sub.3),                                               2.92(br, 1H, OH),                                                             4.84(s, 1H, CHOH),                                                            7.32(s, 4H, Benzene ring),                                                    8.88(s, 1H, Pyrimidine ring),                                                 8.98(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3 !                                                                 MS(EI) m/z; 276(M.sup.+, 41), 261(13),                                        243(8), 221(base peak), 219(99),                                              185(73), 57(95)                                                         105   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.2 1.5474                                1.43(s, 9H, C(CH.sub.3).sub.3),                                               4.39(br, 1H, OH),                                                             6.41(s, 1H, CHOH),                                                            7.15(s, 4H, Benzene ring),                                                    8.30(s, 1H, Pyrimidine ring),                                                 8.76(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3 !                                                           106   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.5 1.5020                                0.49˜0.74(m, 4H, cyclopropane(methylene))                               1.23-1.44(m, 4H, cyclopropane(methine))                                       3.00(br, 1H, OH),                                                             4.70˜4.89(m, 1H, φCHOH)                                             9.11(s, 1H, Pyrimidine ring),                                                 9.19(s, 1H, Pyrimidine ring),                                                  CDCl.sub.3)                                                            107   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.1 1.4347                                1.55(d, J=6Hz, 3H, CH.sub.3)                                                  2.4˜3.0(br s, 1H, OH)                                                   5.1˜5.6(m, 1H, CH)                                                      9.12(s, 1H, Pyrimidine ring)                                                  9.22(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           108   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.5 1.5554                                0.74(s, 9H, C(CH.sub.3).sub.3)                                                3.23(br s, 1H, OH)                                                            4.22(s, 1H, φCH)                                                          6.92˜7.26(m, 3H, Benzene ring)                                          8.85(s, 1H, Pyrimidine ring)                                                  8.97(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           109   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.3 1.5464                                1.43(s, 9H, C(CH.sub.3).sub.3)                                                4.83(br s, 1H, OH)                                                            6.45(s, 1H, φCH)                                                          6.76˜7.27(m, 3H, Benzene ring)                                          8.24(s, 1H, Pyrimidine ring)                                                  8.76(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           110   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.6 1.4982                                1.78(s, 6H, CH.sub.3 × 2),                                              3.05(br. s, 1H, OH)                                                           9.17(s, 1H, Pyrimidine ring)                                                  9.32(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           111   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.8 1.4798                                0.70˜1.19(m, 3H, CH.sub.3)                                              1.19˜2.00(m, 4H, CHCH.sub.2 CH.sub.2 CH.sub.3)                          2.4˜3.1(br s, 1H, OH)                                                   5.0˜5.5(m, 1H, CH)                                                      9.09(s, 1H, Pyrimidine ring)                                                  9.12(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           112   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.9 1.4845                                1.05(t, J=7Hz, 3H, CH.sub.2 CH.sub.3)                                         1.74(br q, J=7Hz, 2H, CHCH.sub.2 CH.sub.3)                                    2.91(d, J=3Hz, 1H, OH)                                                        4.85˜5.35(m, 1H, CH)                                                    9.06(s, 1H, Pyrimidine ring)                                                  9.10(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           113   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 142-144° C.                                  0.21˜0.74(m, 4H, cyclo-propyl CH.sub.2)                                 0.94˜1.46(m, 1H, cyclo-propyl CH)                                       3.10(br. s, 1H, OH)                                                           4.25(d, J=7Hz, 1H, φCH)                                                   7.33(d, J=9Hz, 2H, Benzene ring)                                              7.51(d, J=9Hz, 2H, Benzene ring)                                              8.96(s, 1H, Pyrimidine ring)                                                  9.01(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           114   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.8 1.4822                                0.99(t, J=6Hz, 6H, CH(CH.sub.3).sub.2)                                        2.00(qq, J=6Hz, 1H, CH(CH.sub.3).sub.2)                                       2.8˜3.8(br s, 1H, OH)                                                   4.99(br d, 1H, CHOH)                                                          9.10(s, 2H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           115   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 90-92° C.                                    1.41(s, 9H, C(CH.sub.3).sub.3)                                                3.78(s, 3H, OCH.sub.3)                                                        4.80(br s, 1H, OH)                                                            6.48(br s, 1H, CH)                                                            6.84(d, J=9Hz, 2H, Benzene ring)                                              7.20(d, J=9Hz, 2H, Benzene ring)                                              8.58(s, 1H, Pyrimidine ring)                                                  8.88(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           116   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 102-104° C.                                  1.45(s, 9H, C(CH.sub.3).sub.2)                                                3.61(br s, 1H, OH)                                                            3.81(s, 3H, OCH.sub.3)                                                        6.6˜7.6(m, 5H, CH + Benzene ring)                                       8.67(s, 1H, Pyrimidine ring)                                                  9.04(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           117   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 125-127° C.                                  1.36(s, 9H, C(CH.sub.3).sub.3)                                                2.34(s, 3H, CH.sub.3)                                                         4.25(br s, 1H, OH)                                                            6.56(s, 1H, CH)                                                               6.9˜7.6(m, 4H, Benzene ring)                                            8.63(s, 1H, Pyrimidine ring)                                                  8.90(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           118   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.21.5 1.5574                                1.43(s, 9H, C(CH.sub.3).sub.3)                                                2.30(s, 3H, CH.sub.3)                                                         4.8˜5.3(m, 1H, OH)                                                      6.45(br s, 1H, CH)                                                            6.8˜7.5(m, 4H, Benzene ring)                                            8.48(s, 1H, Pyrimidine ring)                                                  8.85(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           119   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.3 1.5563                                3.40(br s, 1H, OH)                                                            6.34(s, 1H, φCH)                                                          7.29(s, 4H, Benzene ring)                                                     9.09(s, 1H, Pyrimidine ring)                                                  9.14(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           120   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.1 1.4616                                1.53(d, J=6Hz, 3H, CHCH.sub.3)                                                2.62(br s, 1H, OH)                                                            5.07˜5.58(m, 1H, CHCH.sub.3)                                            9.10(s, 1H, Pyrimidine ring)                                                  9.18(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           121   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 141-142° C.                                  3.42(br d, J=5Hz, 1H, OH)                                                     6.58(d, J=5Hz, 1H, φCH)                                                   7.30˜7.45(m, 3H, Benzene ring)                                          8.82(s, 1H, Pyrimidine ring)                                                  9.20(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           122   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.1 1.5160                                1.57(d, J=6Hz, 3H, CHCH.sub.3)                                                3.12˜3.78(br s, 1H, OH)                                                 5.41(d, 1, J=3, 6Hz, 1H, CHCH.sub.3)                                          9.07(s, 1H, Pyrimidine ring)                                                  9.17(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           123   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.0 1.5566                                4.79˜5.04(m, 1H, OH)                                                    6.23(br s, 1H, φCH)                                                       7.17(br s, 5H, Benzene ring)                                                  8.82(s, 1H, Pyrimidine ring)                                                  8.97(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           124   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.5 1.5394                                3.68(d, J=6Hz, 1H, OH)                                                        6.20˜6.40(m, 1H, CHOH)                                                  6.90˜7.53(m, 4H, Benzene ring)                                          9.06(s, 2H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           125   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.7 1.5434                                3.38-4.08(br s, 1H, OH)                                                       6.55(s, 1H, CHOH)                                                             6.68-7.58(m, 4H, Benzene ring)                                                9.06(s, 2H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           126   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.20.5 1.5378                                4.20-4.41(br m, 1H, OH)                                                       6.53-6.67(m, 1H, CHOH)                                                        7.12-7.56(m, 4H, Benzene ring)                                                8.73(s, 1H, Pyrimidine ring)                                                  9.00(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           127   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.8 1.5402                                4.22-4.43(br m, 1H, OH)                                                       6.21-6.35(m, 1H, CHOH)                                                        7.06-7.35(m, 4H, Benzene ring)                                                8.99(s, 1H, Pyrimidine ring)                                                  9.02(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           128   .sup.1 H-NMR δ (ppm)  solvent!;                                                                mp 66-68° C.                                    3.10-3.50(br m, 1H, OH)                                                       6.23-6.32(m, 1H, CHOH)                                                        6.97-7.48(m, 3H, Benzene ring)                                                8.98(s, 1H, Pyrimidine ring)                                                  9.10(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           129   .sup.1 H-NMR δ (ppm)  solvent!;                                                                n.sub.D.sup.19.7 1.5438                                3.40-3.80(br s, 1H, OH)                                                       6.33(s, 1H, CHOH)                                                             6.74-7.60(m, 4H, Benzene ring)                                                9.01(s, 1H, Pyrimidine ring)                                                  9.09(s, 1H, Pyrimidine ring)                                                   CDCl.sub.3 !                                                           ______________________________________                                    

                  TABLE 3-1                                                       ______________________________________                                         ##STR32##                                                                    Comp. No.                                                                             R1, R2, Ra;      Physical properties                                  ______________________________________                                        201     CF.sub.3, Me, OMe;                                                                             bp 93-97° C./3.5 Torr                         202     CF.sub.3, Me, OEt;                                                                             bp 82-83° C./0.2 Torr                         203     CF.sub.2 Cl, Me, OEt;                                                                          bp 95-118° C./1.6 Torr                        204     CF.sub.2 Cl, Bu.sup.tert, OEt;                                                                 bp 105-107° C./2.0 Torr                       205     CF.sub.2 CF.sub.3, Me, OEt;                                                                    bp 98° C./2.2 Torr                            206     4-Cl-Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                          mp 102-104° C.                                207     CF.sub.2 Cl, Pr.sup.cyclo, OEt;                                                                n.sub.D.sup.20.6 1.4787                              208     2,4-Cl.sub.2 -Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                 n.sub.D.sup.19.9 1.5437                              209     4-Cl-Phenyl, Me, NMe.sub.2 ;                                                                   n.sub.D.sup.20.0 1.5964                              210     CF.sub.2 Cl, Et, OEt;                                                                          bp 117-120° C./2.3 Torr                       211     4-Cl-Phenyl, Pr.sup.cyclo, NMe.sub.2 ;                                                         mp 37-39° C.                                  212     4-MeO-Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                         mp 93-95° C.                                  213     CF.sub.2 Cl, Pr.sup.iso, OEt;                                                                  bp 105-115° C./1.7 Torr                       214     2-Me-Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                          mp 90-92° C.                                  215     3-Me-Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                          mp 83-86° C.                                  216     2-MeO-Phenyl, Bu.sup.tert, NMe.sub.2 ;                                                         mp 109-112° C.                                217     CF.sub.2 CF.sub.2 Cl, Me, OEt;                                                                 bp 110-115° C./2.1 Torr                       218     CF.sub.2 Cl, 4-Cl-Phenyl, NMe.sub.2 ;                                                          bp 79-81° C.                                  219     CF.sub.2 Cl, Phenyl, OEt;                                                                      n.sub.D.sup.20.1 1.5395                              220     CF.sub.2 Cl, 4-F-Phenyl, OEt;                                                                  n.sub.D.sup.20.9 1.5233                              221     CF.sub.2 Cl, 2-F-Phenyl, OEt;                                                                  n.sub.D.sup.20.0 1.3808                              222     CF.sub.2 Cl, 3-F-Phenyl, OEt;                                                                  n.sub.D.sup.19.7 1.4900                              223     CF.sub.2 Cl, 2-Cl-Phenyl, OEt;                                                                 n.sub.D.sup.19.9 1.5306                              224     CF.sub.2 Cl, 3-Cl-Phenyl, OEt;                                                                 n.sub.D.sup.19.9 1.5578                              225     CF.sub.2 Cl, 3,4-Cl.sub.2 -Phenyl, OEt;                                                        n.sub.D.sup.19.9 1.l5578                             226     CHFCl, Pr.sup.n, OEt;                                                                          n.sub.D.sup.19.8 1.4770                              227     CF.sub.2 H, Pr.sup.n, OEt;                                                                     n.sub.D.sup.19.9 1.4580                              228     CF.sub.2 Cl, 2-Me-Phenyl, OEt;                                                                 n.sub.D.sup.20.3 1.5350                              ______________________________________                                    

                  TABLE 3-2                                                       ______________________________________                                         ##STR33##                                                                    Comp.                                                                         No.   R1, R2;        Physical properties                                      ______________________________________                                        301   CF.sub.2 Cl, Bu.sup.tert ;                                                                   bp 54-57° C./5.0 Torr                             302   CF.sub.2 CF.sub.3, Bu.sup.tert ;                                                             .sup.1 H-NMR δ (ppm)  solvent!; 1.22(s,                                 9H, t-Bu), 6.05(s, 1H, CH), 13.0˜                                       14.0(br s, 1H, OH,  CDCl.sub.3 ! liquid.                 303   4-Cl-Phenyl, Bu.sup.tert ;                                                                   n.sub.D.sup.20.0 1.5012                                  304   CF.sub.2 CF.sub.3, Me;                                                                       bp 105-115° C.                                    305   CF.sub.2 Cl, Pr.sup.cyclo ;                                                                  n.sub.D.sup.20.6 1.4788                                  306   2,4-Cl.sub.2 -Phenyl, Bu.sup.tert ;                                                          n.sub.D.sup.19.9 1.5690                                  307   CF.sub.2 Cl, Et;                                                                             bp 74-78° C./20 Torr                              308   CF.sub.2 Cl, Pr.sup.n ;                                                                      bp 84° C./17 Torr                                 309   4-Cl-Phenyl, Pr.sup.cyclo;                                                                   mp 73-75° C.                                      310   CF.sub.2 Cl, Pr.sup.iso ;                                                                    bp 42-43° C./3.0 Torr                             311   4-MeO-Phenyl, Bu.sup.tert ;                                                                  mp 50-52° C.                                      312   2-Me-Phenyl, Bu.sup.tert ;                                                                   n.sub.D.sup.21.5 1.4882                                  313   3-Me-Phenyl, Bu.sup.tert ;                                                                   n.sub.D.sup.21.4 1.5564                                  314   4-CF.sub.3 -Phenyl, Bu.sup.tert ;                                                            mp 55-58° C.                                      315   2-F-Phenyl, Bu.sup.tert ;                                                                    n.sub.D.sup.20.3 1.5488                                  316   2-MeO-Phenyl, Bu.sup.tert ;                                                                  n.sub.D.sup.20.4 1.5622                                  317   2,4-Cl.sub.2 -Phenyl, Me;                                                                    mp 30-31° C.                                      318   CF.sub.2 Cl, 4-Cl-Phenyl;                                                                    mp 50-51° C.                                      319   3-CF.sub.3 -Phenyl, Bu.sup.tert ;                                                            .sup.1 H-NMR δ (ppm)  solvent!; 1.27(s,                                 9H, t-Bu), 6.36(s, 1H, olefin), 7.30˜                                   8.40(m, 4H, benzene ring), 16.56(s,                                           1H, enol OH)  CDCl.sub.3 ! liquid.                       320   CF.sub.2 Cl, 1-Me-Pr.sup.cyclo ;                                                             bp 59-63° C./2.0 Torr                             321   CF.sub.2 CF.sub.2 Cl, Me;                                                                    bp 120-128° C.                                    322   CF.sub.2 Cl, 2,4-Cl.sub.2 -Phenyl;                                                           n.sub.D.sup.21.7 1.5828                                  323   CF.sub.2 Br, Me;                                                                             bp 100-105° C.                                    324   CF.sub.2 Cl, 4-F-Phenyl;                                                                     mp 48-50° C.                                      325   CF.sub.2 Cl, Phenyl;                                                                         mp 29-30° C.                                      326   CF.sub.2 Cl, 2-F-Phenyl;                                                                     n.sub.D.sup.19.9 1.5554                                  327   CF.sub.2 Cl, 3-F-Phenyl;                                                                     mp 46-48° C.                                      328   CF.sub.2 Cl, 2-Cl-Phenyl;                                                                    n.sub.D.sup.19.9 1.5630                                  329   CF.sub.2 Cl, 3-Cl-Phenyl;                                                                    n.sub.D.sup.19.9 1.5807                                  330   CF.sub.2 Cl, 3,4-Cl.sub.2 -Phenyl;                                                           mp 41-43° C.                                      331   CHFCl, Pr.sup.n ;                                                                            bp 94-100° C./20 Torr                             332   CF.sub.2 H, Pr.sup.n ;                                                                       bp 74-76° C./20 Torr                              333   CF.sub.2 Cl, 2-Me-Phenyl;                                                                    n.sub.D.sup.19.9 1.5566                                  ______________________________________                                         Tables 41, 42 and 43 show the compounds of the present invention which ca     be synthesized in accordance with the abovementioned schemes and Examples     including those synthesized in the preceding Examples. However, it should     be understood that the present invention is by no means restricted by suc     specific examples.                                                       

                  TABLE 4-1                                                       ______________________________________                                         ##STR34##                                                                     ##STR35##                                                                     ##STR36##                                                                     ##STR37##                                                                     ##STR38##                                                                     ##STR39##                                                                     ##STR40##                                                                     ##STR41##                                                                     ##STR42##                                                                     ##STR43##                                                                     ##STR44##                                                                     ##STR45##                                                                     ##STR46##                                                                     ##STR47##                                                                     ##STR48##                                                                     ##STR49##                                                                     ##STR50##                                                                     ##STR51##                                                                     ##STR52##                                                                     ##STR53##                                                                     ##STR54##                                                                     ##STR55##                                                                     ##STR56##                                                                     ##STR57##                                                                     ##STR58##                                                                     ##STR59##                                                                     ##STR60##                                                                     ##STR61##                                                                     ##STR62##                                                                     ##STR63##                                                                     ##STR64##                                                                     ##STR65##                                                                     ##STR66##                                                                     ##STR67##                                                                     ##STR68##                                                                     ##STR69##                                                                     ##STR70##                                                                     ##STR71##                                                                     ##STR72##                                                                     ##STR73##                                                                     ##STR74##                                                                     ##STR75##                                                                     ##STR76##                                                                     ##STR77##                                                                     ##STR78##                                                                     ##STR79##                                                                     ##STR80##                                                                     ##STR81##                                                                     ##STR82##                                                                     ##STR83##                                                                     ##STR84##                                                                     ##STR85##                                                                     ##STR86##                                                                     ##STR87##                                                                     ##STR88##                                                                     ##STR89##                                                                     ##STR90##                                                                    wherein R2 is selected from the following group.                              ______________________________________                                        R2                                                                            ______________________________________                                        Me, Et, Pr, Pr.sup.iso, Pr.sup.cyclo, Bu, Bu.sup.sec, Bu.sup.iso,             Bu.sup.tert,                                                                  Bu.sup.cyclo, Pn, Pn.sup.neo, Pn.sup.iso, Pn.sup.cyclo, Hex,                  Hex.sup.cyclo,                                                                C(Me).sub.2 (CH.sub.2 F), CF.sub.3, CH.sub.2 CF.sub.3, Ph, 2-Cl-Ph,           3-Cl-Ph, 4-Cl-Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-CF.sub.3 -Ph,                     3-CF.sub.3 -Ph, 4-CF.sub.3 -Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph,                    2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF.sub.3 O-Ph,                                3-CF.sub.3 O-Ph, 4-CF.sub.3 O-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph,                  2,4-Cl.sub.2 -Ph, 3,4-Cl.sub.2 -Ph, 2,6-Cl.sub.2 -Ph, 2-F-4-Cl-Ph,            2,4-F.sub.2 -Ph, 3,4-F.sub.2 -Ph, 2,5-Cl.sub.2 -Ph, 2,3-Cl.sub.2 -Ph,         2,6-F.sub.2 -Ph, CH.sub.2 Br                                                  3,5-Cl.sub.2 -Ph, 2-Me-4-Cl-Ph, 2-Me-4-F-Ph, 1-MeSO.sub.2 -Et,                1-Me-Pr.sup.cyclo, 1-FPr.sup.cyclo, 1-ClPr.sup.cyclo, 1-MeSPr.sup.cyclo,      1-EtSPr.sup.cyclo, CH.sub.2 Cl, CF(Me).sub.2, 1-Pr.sup.cyclo -Et,             CH.sub.2 CHCH.sub.2, CH.sub.2 CCH,                                            CH(Me)CCH, C(Me).sub.2 CCH,                                                   CH(Me)CHCH.sub.2, 4-Bu.sup.tert -Ph, 3-Bu.sup.tert -Ph,                       2-Bu.sup.tert -Ph, 2-Et-Ph, 3-Et-Ph, 4-Et-Ph, 2-Pr-Ph, 3-Pr-Ph,               4-Pr-Ph, 2-Bu-Ph, 3-Bu-Ph, 4-Bu-Ph, 2-EtO-Ph,                                 2-Pr.sup.iso O-Ph, 2-PrO-Ph,                                                  ______________________________________                                    

                  TABLE 4-2                                                       ______________________________________                                         ##STR91##                                                                     ##STR92##                                                                     ##STR93##                                                                     ##STR94##                                                                     ##STR95##                                                                     ##STR96##                                                                     ##STR97##                                                                     ##STR98##                                                                     ##STR99##                                                                     ##STR100##                                                                    ##STR101##                                                                    ##STR102##                                                                    ##STR103##                                                                    ##STR104##                                                                    ##STR105##                                                                    ##STR106##                                                                    ##STR107##                                                                    ##STR108##                                                                    ##STR109##                                                                    ##STR110##                                                                    ##STR111##                                                                    ##STR112##                                                                    ##STR113##                                                                    ##STR114##                                                                    ##STR115##                                                                    ##STR116##                                                                    ##STR117##                                                                    ##STR118##                                                                    ##STR119##                                                                    ##STR120##                                                                    ##STR121##                                                                    ##STR122##                                                                    ##STR123##                                                                    ##STR124##                                                                    ##STR125##                                                                    ##STR126##                                                                    ##STR127##                                                                    ##STR128##                                                                    ##STR129##                                                                    ##STR130##                                                                    ##STR131##                                                                    ##STR132##                                                                    ##STR133##                                                                    ##STR134##                                                                    ##STR135##                                                                    ##STR136##                                                                    ##STR137##                                                                    ##STR138##                                                                    ##STR139##                                                                    ##STR140##                                                                    ##STR141##                                                                    ##STR142##                                                                    ##STR143##                                                                    ##STR144##                                                                    ##STR145##                                                                    ##STR146##                                                                    ##STR147##                                                                   ______________________________________                                        R2                                                                            ______________________________________                                        Me, Et, Pr, Pr.sup.iso, Pr.sup.cyclo, Bu, Bu.sup.sec, Bu.sup.iso,             Bu.sup.tert,                                                                  Bu.sup.cyclo, Pn, Pn.sup.neo, Pn.sup.iso, Pn.sup.cyclo, Hex,                  Hex.sup.cyclo,                                                                C(Me).sub.2 (CH.sub.2 F), CF.sub.3, CH.sub.2 CF.sub.3, Ph, 2-Cl-Ph,           3-Cl-Ph, 4-Cl-Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-CF.sub.3 -Ph,                     3-CF.sub.3 -Ph, 4-CF.sub.3 -Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph,                    2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF.sub.3 O-Ph,                                3-CF.sub.3 O-Ph, 4-CF.sub.3 O-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph,                  2,4-Cl.sub.2 -Ph, 3,4-Cl.sub.2 -Ph, 2,6-Cl.sub.2 -Ph, 2-F-4-Cl-Ph,            2,4-F.sub.2 -Ph, 3,4-F.sub.2 -Ph, 2,5-Cl.sub.2 -Ph, 2,3-Cl.sub.2 -Ph,         2,6-F.sub.2 -Ph, CH.sub.2 Br                                                  3,5-Cl.sub.2 -Ph, 2-Me-4-Cl-Ph, 2Me-4-F-Ph, 1-MeSO.sub.2 -Et,                 1-Me-Pr.sup.cyclo, 1-FPr.sup.cyclo, 1-ClPr.sup.cyclo, 1-MeSPr.sup.cyclo,      1-EtSPr.sup.cyclo, CH.sub.2 Cl, CF(Me).sub.2, 1-Pr.sup.cyclo -Et,             CH.sub.2 CHCH.sub.2, CH.sub.2 CCH,                                            CH(Me)CCH, C(Me).sub.2 CCH,                                                   CH(Me)CHCH.sub.2, 4-Bu.sup.tert -Ph, 3-Bu.sup.tert -Ph,                       2-Bu.sup.tert -Ph, 2-Et-Ph, 3-Et-Ph, 4-Et-Ph, 2-Pr-Ph, 3-Pr-Ph,               4-Pr-Ph, 2-Bu-Ph, 3-Bu-Ph, 4-Bu-Ph, 2-EtO-Ph,                                 2-Pr.sup.iso O-Ph, 2-PrO-Ph,                                                  ______________________________________                                    

                  TABLE 4-3                                                       ______________________________________                                         ##STR148##                                                                    ##STR149##                                                                    ##STR150##                                                                    ##STR151##                                                                    ##STR152##                                                                    ##STR153##                                                                    ##STR154##                                                                    ##STR155##                                                                    ##STR156##                                                                    ##STR157##                                                                    ##STR158##                                                                    ##STR159##                                                                    ##STR160##                                                                    ##STR161##                                                                    ##STR162##                                                                    ##STR163##                                                                    ##STR164##                                                                    ##STR165##                                                                    ##STR166##                                                                    ##STR167##                                                                    ##STR168##                                                                    ##STR169##                                                                    ##STR170##                                                                    ##STR171##                                                                    ##STR172##                                                                    ##STR173##                                                                    ##STR174##                                                                    ##STR175##                                                                    ##STR176##                                                                    ##STR177##                                                                   ______________________________________                                        R2                                                                            ______________________________________                                        Me, Et, Pr, Pr.sup.iso, Pr.sup.cyclo, Bu, Bu.sup.sec, Bu.sup.iso,             Bu.sup.tert,                                                                  Bu.sup.cyclo, Pn, Pn.sup.neo, Pn.sup.iso, Pn.sup.cyclo, Hex,                  Hex.sup.cyclo,                                                                C(Me).sub.2 (CH.sub.2 F), CF.sub.3, CH.sub.2 CF.sub.3, Ph, 2-Cl-Ph,           3-Cl-Ph, 4-Cl-Ph, 2-F-Ph, 3-F-Ph, 4-F-Ph, 2-CF.sub.3 -Ph,                     3-CF.sub.3 -Ph, 4-CF.sub.3 -Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph,                    2-MeO-Ph, 3-MeO-Ph, 4-MeO-Ph, 2-CF.sub.3 O-Ph,                                3-CF.sub.3 O-Ph, 4-CF.sub.3 O-Ph, 2-Br-Ph, 3-Br-Ph, 4-Br-Ph,                  2,4-Cl.sub.2 -Ph, 3,4-Cl.sub.2 -Ph, 2,6-Cl.sub.2 -Ph, 2-F-4-Cl-Ph,            2,4-F.sub.2 -Ph, 3,4-F.sub.2 -Ph, 2,5-Cl.sub.2 -Ph, 2,3-Cl.sub.2 -Ph,         2,6-F.sub.2 -Ph, CH.sub.2 Br                                                  3,5-Cl.sub.2 -Ph, 2-Me-4-Cl-Ph, 2Me-4-F-Ph, 1-MeSO.sub.2 -Et,                 1-Me-Pr.sup.cyclo, 1-FPr.sup.cyclo, 1-ClPr.sup.cyclo, 1-MeSPr.sup.cyclo,      1-EtSPr.sup.cyclo, CH.sub.2 Cl, CF(Me).sub.2, 1-Pr.sup.cyclo -Et,             CH.sub.2 CHCH.sub.2, CH.sub.2 CCH,                                            CH(Me)CCH, C(Me).sub.2 CCH,                                                   CH(Me)CHCH.sub.2, 4-Bu.sup.tert -Ph, 3-Bu.sup.tert -Ph,                       2-Bu.sup.tert -Ph, 2-Et-Ph, 3-Et-Ph, 4-Et-Ph, 2-Pr-Ph, 3-Pr-Ph,               4-Pr-Ph, 2-Bu-Ph, 3-Bu-Ph, 4-Bu-Ph, 2-EtO-Ph,                                 2-Pr.sup.iso O-Ph, 2-PrO-Ph,                                                  ______________________________________                                    

The symbols in the tables have the following meanings.

Ph: Phenyl

Me: CH₃

Et: C₂ H₅

Pr, Pr^(n) : CH₂ CH₂ CH₃

Pr^(iso) : CH(CH₃ )₂

Pr^(cyclo) : CH (CH₂)₂

Bu, Bu^(n) : CH₂ CH₂ CH₂ CH₃

Bu^(sec) : CH(CH₃)C₂ H₅

Bu^(iso) : CH₂ CH(CH₃)₂

Bu^(tert) : C(CH₃)₃

Bu^(cyclo) : CH(CH₂)₃

Pn, Pn^(n) : CH₂ CH₂ CH₂ CH₂ CH₃

Pn^(cyclo) : CH(CH₂)₄

Pn^(iso) : CH₂ CH₂ CH(CH₃).sub.

Pn^(neo) : CH₂ C(CH₃)₃

Hex, Hex^(n) : CH₂ (CH₂)₄ CH₃

Hep, Hep^(n) : CH₂ (CH₂)₅ CH₃

Oct, Oct^(n) : CH₂ (CH₂)₆ CH₃

4-Cl--Ph: 4-Cl-Phenyl

When the compound of the present invention is used as a herbicide or asa plant growth regulator, it is usually mixed with a suitable carrier,for instance, a solid carrier such as clay, talc, bentonite, urea,ammonium sulfate, walnut powder, diatomaceous earth or white carbon, ora liquid carrier such as water, an alcohol (such as isopropanol,butanol, ethylene glycol, benzyl alcohol or furfuryl alcohol), anaromatic hydrocarbon (such as toluene, xylene or methylnaphthalene), anether (such as anisole), a vegetable oil (such as soybean oil orcottonseed oil), a ketone (such as cyclohexanone or isophorone), anester (such as butyl acetate), an acid amide (such asN-methylpyrrolidone) or a hologenated hydrocabron (such aschlorobenzene). If desired, a surfactant, an emulsifier, a dispersingagent, a penetrating agent, a spreader, a thickner, a antifreezingagent, an anticaking agent, or a stabilizer may be added to prepare anoptional formulation such as a liquid formulation, an emulsifiableconcentrate, a wettable powder, a dry flowable, a flowable, a dust or agranule.

Further, the compound of the present invention may be combined withother herbicides, various insecticides, miticides, nematicides,fungicides, plant growth regulators, synergists, fertilizers or soilconditioning materials at the time of the preparation of theformulations or at the time of the application, as the case requires.

Particularly, combined use of the compound of the present invention withanother agricultural chemical can be expected to result in lower costattributable to reduction in the dose, a broader spectrum and a higherherbicidal or plant growth regulating effect attributable to synergisticaction of the combined chemical. In such a case, the compound of thepresent invention can be combined with plural known agriculturalchemicals simultaneously. The agricultural chemicals which may be usedin combination with the compound of the present invention, may be, forexample, compounds disclosed in Farm Chemicals Handbook (1994).

The dose of the compound of the present invention varies depending uponthe application site, the season for application, the manner ofapplication, weather conditions, the formulation, soil conditions, thetype of crop plants and the like. However, it is usually within a rangeof from 0.000001 to 10 kg, preferably from 0.00001 to 5 kg per hectar(ha) as the amount of the active ingredient. However, when the compoundof the present invention is used for promoting plant seed germination orinitial growth, it is preferred to adjust the active ingredientconcentration to a level of from 0.01 to 100 ppb before application.

Now, examples of formulations of the compounds of the present inventionwill be given. However, it should be understood that the presentinvention is by no means restricted to such specific examples. In thefollowing Formulation Examples, "parts" means parts by weight.

    ______________________________________                                         Wettable powder!                                                             ______________________________________                                        Compound of the present invention                                                                     0.1-80 parts                                          Solid carrier           10-90 parts                                           Surfactant              1-10 parts                                            Other                   1-5 parts                                             ______________________________________                                    

As the others, for example, an anticaking agent may be mentioned.

    ______________________________________                                         Emulsifiable Concentrate!                                                    Compound of the present invention                                                                     0.1-30 parts                                          Liquid carrier          30-95 parts                                           Surfactant              5-15 parts                                             Flowable!                                                                    Compound of the present invention                                                                     0.1-70 parts                                          Liquid carrier          15-65 parts                                           Surfactant              5-12 parts                                            Others                  5-30 parts                                            ______________________________________                                    

As the others, for example, an antifreezing agent and a thickner may bementioned.

    ______________________________________                                         Granular wettable powder (dry flowable)!                                     Compound of the present invention                                                                     0.1-90 parts                                          Solid carrier           10-70 parts                                           Surfactant              1-20 parts                                             Granule!                                                                     Compound of the present invention                                                                     0.0001-10 parts                                       Solid carrier           90-99.9999 parts                                      Others                  0.1-10 parts                                           Liquid formulation!                                                          Compound of the present invention                                                                     0.00001-30 parts                                      Liquid carrier          0.1-50 parts                                          Water                   50-99.99 parts                                        Others                  0-10 parts                                             Formulation for wiping!                                                      Compound of the present invention                                                                     1-50 parts                                            Liquid carrier          30-95 parts                                           Thickner                5-50 parts                                             Formulation for trunk injection!                                             Compound of the present invention                                                                     0.01-30 parts                                         Liquid carrier          70-99.99 parts                                         Formulation Example 1! Wettable powder                                       Compound No. 5 of the present invention                                                               50 parts                                              Zeeklite PFP (tradename for a kaolin-type                                                             43 parts                                              clay, manufactured by Zeeklite Industries,                                    Co., Ltd.)                                                                    Sorpol 5050 (tradename for an anionic                                                                 2 parts                                               surfactant, manufactured by Toho Chemical                                     Industry Co., Ltd.)                                                           Lunox 1000C (tradename for an anionic                                                                 3 parts                                               surfactant, manufactured by Toho Chemical                                     Industry Co., Ltd.)                                                           Carplex #80 (anticaking agent) (tradename                                                             2 parts                                               for a white carbon, manufactured by                                           Shionogi Pharmaceutical Co., Ltd.)                                            ______________________________________                                    

The above ingredients are homogeneously pulverized and mixed to form awettable powder.

    ______________________________________                                         Formulation Example 2! Emulsifiable concentrate                              ______________________________________                                        Compound No. 24 of the present invention                                                                 3 parts                                            Xylene                    76 parts                                            Isophorone                15 parts                                            Sorpol 3005X (tradename for a mixture of                                                                 6 parts                                            a nonionic surfactant and an anionic                                          surfactant, manufactured by Toho Chemical                                     Industry Co., Ltd.)                                                           ______________________________________                                    

The above ingredients are homogeneously mixed to form an emulsifiableconcentrate.

    ______________________________________                                         Formulation Example 3! Flowable                                              ______________________________________                                        Compound No. 103 of the present invention                                                               35 parts                                            Agrizole S-711 (tradename for a nonionic                                                                8 parts                                             surfactant, manufactured by Kao Corporation)                                  Lunox 1000C (tradename for an anionic                                                                   0.5 part.sup.                                       surfactant, manufactured by Toho Chemical                                     Industry Co., Ltd.)                                                           1% Rodopol water (tradename for a thickner,                                                             20 parts                                            manufactured by Rhone-Poulenc)                                                Ethylene glycol (antifreezing agent)                                                                    8 parts                                             Water                     28.5 parts                                          ______________________________________                                    

The above ingredients are homogeneously mixed to obtain a flowable.

    ______________________________________                                         Formulation Example 4! Granular wettable powder (dry                         flowable)                                                                     ______________________________________                                        Compound No. 111 of the present invention                                                                 75 parts                                          Isoban No. 1 (tradename for an anionic                                                                    10 parts                                          surfactant, manufactured by Kuraray Isoprene                                  Chemical Co., Ltd.)                                                           Vanilex N (tradename for an anionic                                                                       5 parts                                           surfactant, manufactured by Sanyo-Kokusaku                                    Pulp Co., Ltd.)                                                               Carplex #80 (tradename; for a white carbon,                                                               10 parts                                          manufactured by Shionogi Pharmaceutical                                       Co., Ltd.)                                                                    ______________________________________                                    

The above ingredients were homogeneously pulverized and mixed to form adry flowable.

    ______________________________________                                         Formulation Example 5! Granule                                               ______________________________________                                        Compound No. 123 of the present invention                                                               0.1 part.sup.                                       Bentonite                 50.0 parts                                          Talc                      44.9 parts                                          Toxanone GR-31A (tradename for an anionic                                                               5 parts                                             surfactant, manufactured by Sanyo Chemical                                    Industries LTD.)                                                              ______________________________________                                    

The above ingredients are homogeneously mixed and pulverized, and afteran addition of a small amount of water, the mixture was stirred, mixedand granulated by an extrusion-type granulating machine, followed bydrying to obtain a granule.

    ______________________________________                                         Formulation Example 6! Liquid formulation                                    ______________________________________                                        Compound No. 101 of the present invention                                                              3 parts                                              1-methoxy-2-propanol    20 parts                                              Water                   77 parts                                              ______________________________________                                    

The above ingredients are into a homogeneous solution to obtain a liquidformulation.

    ______________________________________                                         Formulation Example 7! Liguid formulation                                    ______________________________________                                        Compound No. 103 of the present                                                                       0.0001 part.sup.                                      invention                                                                     1-methoxy-2-propanol    1.0 part.sup.                                         Water                   98.9999 parts                                         ______________________________________                                    

The above ingredients are mixed into a homogeneous solution to obtain aliquid formulation.

    ______________________________________                                         Formulation Example 8! Formulation for wiping                                Compound No. 124 of the present invention                                                                10 parts                                           Thixogel VP (tradename, manufactured                                                                     10 parts                                           by Nissan Gardlar Shokubai K.K.)                                              Xylene                     80 parts                                            Formulation Example 9! Formulation for wiping                                Compound No. 119 of the present invention                                                                15 parts                                           Thixogel VP (tradename, manufactured                                                                     10 parts                                           by Nissan Gardlar Shokubai K.K.)                                              Highsol 100 (tradename, manufactured                                                                     75 parts                                           by Nisseki Chemical K.K.)                                                      Formulation Example 10! Formulation for trunk injection                      Compound No. 114 of the present invention                                                                 6 parts                                           Isopropanol                94 parts                                            Formulation Example 11! Formulation for trunk injection                      Compound No. 106 of the present invention                                                                 5 parts                                           Ethanol                    95 parts                                           ______________________________________                                    

The above wettable powders, emulsifiable concentrates, flowables andgranular wettable powders are diluted with water from 50 to 1,000 timesbefore application, and are applied at a dose of from 0.000001 to 10 kga hectar (ha) as the amount of the active ingredient.

Now, the usefulness of the compounds of the present invention asherbicides and plant growth regulators will be described in detail withreference to the following Test Examples.

TEST EXAMPLE 1!

Test on the herbicidal effects in pre-emergence treatment on weeds undersubmerged conditions

Wagner pots of 1/5000 a were filled with alluvial soil, and water wasadmixed to form a submerged state with a water depth of 4 cm. Seeds ofbarnyardgrass, bulrush, ducksalad and toothcup, and tubers of japaneseribbon wapato and perennial flat sedge were planted in the pots. Then,rice seedlings of 2 leaf stage were transplanted in the pots. The potswere placed in a greenhouse at a temperature of from 25° to 30° C., toculture the plants. A day after the planting, compounds of the presentinvention formulated in accordance with Formulation Examples wereapplied to the water surfaces at predetermined dose. Three weeks afterthe application, the herbicidal effects against various weeds and theinfluences on rice were determined on the basis of the 5-rank gradingsuch that 0 means no effect, and 5 means complete death. The results areshown in Table 5-1. Each Compound No. in Table 5-1 corresponds to thatin Examples, and the symbols in Table 5-1 have the following meanings.

A: barnyardgrass, B: bulrush, C: ducksalad, D: toothcup, E: japaneseribbon wapato, F: perennial flat sedge, a: rice

TEST EXAMPLE 2!

Test on the herbicidal effects in post-emergence treatment on weedsunder submerged conditions

Wagner pots of 1/5000 a were filled with alluvial soil, and water wasadmixed to form a submerged state with a water depth of 4 cm.

In each of the above pots, seeds of barnyardgrass, bulrush, ducksaladand toothcup were sown, and the pots were placed in a greenhouse at atemperature of from 25° to 30° C. to culture the plants. 14 days afterthe seeding, the compound of the present invention formulated inaccordance with Formulation Examples were applied to the water surfacesat predetermined doses. Three weeks after the application, theherbicidal effect against various weeds were determined on the basis ofthe 5-rank grading such that 0 indicates no effect, and 5 indicatescomplete death. The results are shown in Table 5-2. Each Compound No. inTable 5-2 corresponds to that in Examples, and the symbols in Table 5-2have the following meanings.

A: barnyardgrass, B: bulrush, C: ducksalad, D: toothcup

TEST EXAMPLE 3!

Test on the herbicidal effects in soil treatment

Plastic boxes having a length of 33 cm, a width of 33 cm and a depth of8 cm were filled with diluvial soil, and seeds of barnyardgrass, greenfoxtail, wild oat, blackgrass, velvetleaf, common cocklebur, redrootpigweed, morningglory, persian speedwell, common chickweed, rice, corn,wheat, soybean, cotton and sugar beet were sown and covered with soilthereon in a thickness of about 1.5 cm, and then the compounds of thepresent invention formulated in accordance with Formulation Exampleswere applied onto the surfaces of the soil uniformly at predetermineddoses. Three weeks after the application, the herbicidal effects againsteach weed and the influences on each crop plant were determined on thebasis of the 5-rank grading such that 0 indicates no effect, and 5indicates complete death. The results are shown in Table 5-3.

Each Compound No. in Table 5-3 corresponds to that in Examples, and thesymbols in Table 5-3 have the following meanings.

G: barnyardgrass, H: green foxtail, I: wild oat, J: blackgrass, K:velvetleaf, L: common cocklebur, M: redroot pigweed, N: morningglory, 0:persian speedwell, P: common chickweed, a: rice, b: corn, c: wheat, d:soybean, e: cotton, f: sugar beet

TEST EXAMPLE 4!

Test on the herbicidal effects in foliage treatment

A plastic boxes having a length of 33 cm, a width of 33 cm and a depthof 8 cm were filled with a sterilized diluvial soil, and seeds ofbarnyardgrass, green foxtail, wild oat, blackgrass, velvetleaf, commoncocklebur, redroot pigweed, morningglory, persian speedwell, commonchickweed, rice, corn, wheat, soybean, cotton and sugar beet were sown,and covered with soil in a thickness of about 1.5 cm. And the boxes wereplaced in a greenhouse at a temperature of from 25° to 30° C. for 14days to culture the plants, and the compounds of the present inventionformulated in accordance with Formulation Examples were applied to thefoliages uniformly at predetermined doses. Three weeks after theapplication, the herbicidal effects against each weed and the influenceson each crop plant were determined on the basis of the 5-rank gradingsuch that 0 indicates no effect, and 5 indicated complete death. Theresults are shown in Table 5-4.

Each Compound No. in Table 5-4 corresponds to that in Examples, and thesymbols in Table 5-4 have the following meanings.

G: barnyardgrass, H: green foxtail, I: wild oat, J: blackgrass, K:velvetleaf, L: common cocklebur, M: redroot pigweed, N: morningglory, 0:persian speedwell, P: common chickweed, a: rice, b: corn, c: wheat, d:soybean, e: cotton, f: sugar beet

TEST EXAMPLE 5!

Test on the dwarfing effects in foliage treatment

Plastic pots having an inner diameter of 12 cm and a depth of 11 cm werefilled with a sterilized diluvial soil, and seeds of rice, wheat,bermudagrass or bentgrass were sown in each pot, and were covered withthe soil in a thickness of about 1 cm. The pots were placed in a greenhouse at a temperature of from 25° to 30° C. to culture the plants. Wheneach plant grew to the 1 or 2 leaf stage, the compounds of the presentinvention formulated in accordance with Formulation Examples wereuniformly sprayed on the foliages at predetermined doses in terms of theactive ingredients. Two weeks after the application, the dwarfingeffects on each weed were determined by measuring the plant length andthe plant age in leaf number. The results are shown in Table 5-5. EachCompound No. in Table 5-5 corresponds to that in Examples, and thesymbols in Table 5-5 have the following meanings.

A: rice, B: wheat, C: bermudagrass, D: bentgrass

TEST EXAMPLE 6!

Test on the dwarfing effects under submerged conditions

Plastic pots of 1/10000 a were filled with alluvial soil, and water wasadmixed to form a submerged state with a water depth of of 4 cm. Riceseedlings at about the 2 leaf stage having been raised in a nursery boxwere transplanted in the pots, and the pots were placed in a greenhouseat a temperature of from 25° to 30° C. to culture rice. When rice grewto about the 3.5 leaf stage, the compounds of the present inventionformulated in accordance with Formulation Examples were applied to thewater surfaces at predetermined doses. Two weeks after the application,the dwarfing effects on rice were determined by measuring the plantlength and the plant age in leaf number. The results are shown in Table5-6. Each Compound No. in Table 5-6 corresponds to that in Examples, andthe symbols in Table 5-6 have the following meanings.

E: rice

TEST EXAMPLE 7!

Test on the dwarfing effects in foliage treatment

Plastic pots having an inner diameter of 12 cm and a depth 11 cm werefilled with a sterilized diluvial soil, and seeds of bermudagrass,bentgrass, soybean, cotton or wheat were sown in each pot, and werecovered with the soil in a thickness of about 1 cm. The pots were placedin a greenhouse at a temperature of from 25° to 30° C. to culture theplants. When each plant grew to the 1 to 2 leaf stage, the foliages weresprayed so that the active ingredients would be applied at predetermineddoses. The spray solutions were prepared by formulating the compounds ofthe present invention in accordance with Formulation Examples, and weresprayed onto the entire surfaces of the foliages of each plant by asmall spray. Two weeks after the application, the dwarfing effects oneach plant were determined by measuring the plant length and the plantage in leaf number. The results are shown in Table 5-7.

Each No. in Table 5-7 corresponds to the Compound No. in Examples, andthe symbols in Table 5-7 have the following meanings.

A: bermudagrass, B: bentgrass, C: soybean, D: cotton, E: wheat

TEST EXAMPLE 8!

Test on the dwarfing effects in foliage treatment

Plastic pots having an inner diameter of 12 cm and a depth of 11 cm werefilled with a sterilized diluvial soil, and seeds of bermudagrass,bentgrass, soybean, cotton, wheat or rice were sown in each pot, andcovered with the soil in a thickness of about 1 cm. The pots were placedin a greenhouse at a temperature of from 25 to 30° C. to culture theplants. When each plant grew to the 1 or 2 leaf stage, the foliages wereuniformly sprayed so that the active ingredients would be applied atpredetermined doses. The spray solutions were prepared by formulatingthe compounds of the present invention in accordance with FormulationExamples, and were applied onto the entire surfaces of the foliages ofeach plant by a small spray. Two weeks after the application, thedwarfing effects on each plant were determined by measuring the plantlength and the plant age in leaf number. The results are shown in Table5-8.

Each No. in Table 5-8 corresponds to the Compound No. in Examples, andthe symbols in Table 5-8 have the following meanings.

A: bermudagrass, B: bentgrass, C: soybean, D: cotton, E: wheat, F: rice

                  TABLE 5-1                                                       ______________________________________                                        Test on the herbicidal effects in pre-emergence                               treatment on weeds under submerged conditions                                 No.    Dose (g/a)                                                                             A      B   C     D   E     F   a                              ______________________________________                                        2      20       5      3   0     2   0     0   1                              4      20       2      5   5     5   4     0   0                              5      20       5      4   4     5   0     0   0                              6      20       5      3   5     5   0     0   0                              7      20       4      1   1     5   2     2   0                              8      8.3      2      3   --    --  3     2   0                              9      20       2      3   3     5   2     0   0                              10     20       4      1   1     5   1     2   2                              11     14.8     4      0   1     5   0     0   2                              12     10       3      --  --    3   2     2   0                              13     10       4      2   3     5   1     3   2                              14     10       1      2   3     5   0     0   0                              16     10       0      0   0     2   0     0   0                              17     10       0      0   2     2   0     0   0                              18     10       0      0   --    2   0     2   0                              19     10       0      0   0     2   0     0   0                              20     10       5      5   5     5   0     3   0                              21     10       5      5   5     5   0     2   0                              22     10       5      5   5     5   0     0   2                              23     10       5      5   5     5   0     3   0                              24     10       5      5   5     5   4     3   1                              101    20       5      0   0     2   0     --  1                              102    6.4      0      0   0     0   0     --  0                              103    10       5      5   5     5   5     5   2                              104    20       1      1   1     5   0     0   0                              105    20       5      5   5     5   0     5   0                              106    20       5      5   5     5   5     5   3                              107    20       1      --  --    5   2     2   0                              108    20       --     4   --    5   3     4   0                              109    20       2      4   0     5   --    --  0                              110    5.9      5      2   2     5   0     3   2                              111    10       5      5   5     5   4     5   3                              112    10       5      3   4     5   3     5   3                              113    20       2      2   2     5   1     3   0                              114    10       5      5   5     5   5     5   2                              115    10       2      2   2     2   0     0   0                              116    10       4      5   5     5   0     3   0                              117    10       3      3   4     5   0     0   0                              118    10       5      5   5     5   0     5   0                              119    10       5      5   5     5   2     3   0                              120    10       0      2   S     8   2     0   0                              121    10       5      5   5     5   0     2   0                              122    10       4      2   5     5   0     0   2                              123    10       5      5   5     5   5     3   1                              124    10       5      5   5     5   3     5   0                              ______________________________________                                    

                  TABLE 5-2                                                       ______________________________________                                        Test on the herbicidal effects in post-emergence                              treatment on weeds under submerged conditions                                 No.    Dose (g/a)    A     B       G   D                                      ______________________________________                                        2      20            4     0       0   0                                      4      20            0     4       4   0                                      5      20            0     0       3   5                                      7      20            1     1       1   3                                      8      8.3           2     --      --  5                                      9      20            0     0       1   2                                      10     20            4     1       1   3                                      11     14.8          4     2       3   3                                      12     10            2     --      --  --                                     13     10            4     2       --  5                                      14     10            2     1       4   4                                      16     10            0     0       2   1                                      18     10            0     0       2   0                                      19     10            0     0       2   2                                      20     10            5     3       5   4                                      21     10            3     0       5   4                                      22     10            0     0       2   2                                      23     10            5     5       5   5                                      24     10            5     5       5   5                                      101    20            4     0       0   0                                      103    10            5     5       5   5                                      104    20            0     0       2   5                                      105    20            5     5       5   5                                      106    20            4     4       5   3                                      108    20            3     4       0   5                                      109    20            3     4       0   5                                      110    5.9           3     1       1   2                                      111    10            5     3       5   4                                      112    10            4     2       3   5                                      113    20            1     2       2   4                                      114    10            4     3       5   5                                      116    10            4     2       5   3                                      117    10            2     0       3   4                                      118    10            4     0       3   2                                      119    10            5     2       5   4                                      120    10            1     0       0   0                                      121    10            5     0       4   4                                      122    10            3     2       3   3                                      123    10            5     4       5   5                                      124    10            5     5       5   5                                      ______________________________________                                    

                                      TABLE 5-3                                   __________________________________________________________________________    Test on the herbicidal effects in soil treatment                                 Dose                                                                       No.                                                                              (g/a)                                                                            G H I J K L M N O P a b c d e f                                         __________________________________________________________________________    2  50 3 2 3 2 4 3 2 4 5 5 --                                                                              2 0 2 0 1                                         3  50 0 0 0 0 1 4 5 2 4 5 0 0 0 0 0 1                                         5  50 0 0 0 0 0 0 5 0 5 5 0 0 0 0 0 0                                         6  50 0 0 0 0 2 0 5 0 0 0 0 0 0 0 0 0                                         7  50 8 0 0 3 5 3 5 3 5 5 1 0 0 2 0 4                                         8  20.8                                                                             0 0 0 0 2 0 5 0 3 3 0 0 0 0 0 0                                         9  50 0 0 2 0 4 4 5 0 4 3 0 0 0 0 0 1                                         10 50 5 4 0 0 5 4 5 4 5 5 2 1 0 1 2 3                                         11 37 5 4 3 3 4 4 5 4 5 5 3 2 0 0 0 1                                         13 25 0 1 0 0 1 0 5 2 4 4 0 0 0 0 0 0                                         14 25 0 0 0 0 0 0 4 0 0 3 0 0 0 0 0 1                                         16 25 0 0 0 2 0 0 5 0 5 4 0 0 0 0 0 2                                         18 25 0 0 --                                                                              --                                                                              0 0 4 0 0 3 0 0 0 0 0 0                                         19 25 0 0 --                                                                              --                                                                              0 0 5 0 2 3 0 0 --                                                                              0 0 0                                         20 25 5 4 0 2 0 0 5 0 5 5 0 0 0 0 0 2                                         21 25 0 0 0 0 0 0 5 0 5 5 0 0 0 0 0 0                                         22 25 4 3 3 3 2 4 5 4 5 5 2 1 0 0 1 2                                         23 25 0 0 0 0 0 0 5 2 5 5 0 0 0 0 1 3                                         24 25 5 4 3 5 0 3 5 3 5 5 1 0 2 0 0 5                                         101                                                                              50 5 --                                                                              4 4 5 4 5 4 5 5 --                                                                              2 1 3 2 2                                         102                                                                              16 0 0 0 0 0 0 2 0 0 0 --                                                                              0 0 0 0 0                                         103                                                                              25 5 5 5 4 5 4 5 5 5 5 5 4 3 4 4 4                                         104                                                                              50 4 5 0 0 4 0 5 0 5 3 --                                                                              0 0 1 0 0                                         105                                                                              50 5 5 0 5 3 2 5 5 5 5 --                                                                              0 4 0 0 1                                         106                                                                              50 5 5 5 5 5 5 5 4 5 5 5 3 3 5 3 4                                         108                                                                              50 5 4 3 0 5 3 5 2 5 4 0 0 0 3 1 0                                         109                                                                              50 0 0 0 0 2 0 4 0 5 2 0 0 0 0 0 0                                         110                                                                              15 5 5 2 2 5 4 5 3 5 5 3 1 0 0 1 1                                         111                                                                              25 5 5 2 5 5 4 5 3 5 5 2 1 0 2 0 3                                         112                                                                              25 5 4 3 5 4 5 5 4 5 5 2 1 1 2 1 3                                         114                                                                              25 5 5 0 4 5 5 5 5 5 5 4 3 0 4 3 4                                         116                                                                              25 5 5 4 --                                                                              0 0 4 0 4 4 2 0 0 0 0 2                                         117                                                                              25 0 0 0 --                                                                              0 0 5 0 4 3 0 0 --                                                                              0 0 0                                         118                                                                              25 4 0 --                                                                              --                                                                              0 0 4 0 2 0 0 0 --                                                                              0 0 0                                         119                                                                              25 5 5 0 0 4 4 5 5 5 5 1 0 0 0 0 4                                         121                                                                              25 0 0 0 0 0 0 5 0 5 5 0 0 0 0 0 1                                         122                                                                              25 5 3 0 4 4 2 5 3 5 5 2 0 0 1 0 1                                         123                                                                              25 S 5 3 5 5 5 5 4 5 5 3 3 3 3 3 5                                         124                                                                              25 5 5 3 5 5 5 5 5 5 5 5 3 3 3 4 4                                         __________________________________________________________________________

                                      TABLE 5-4                                   __________________________________________________________________________    Test on the herbicidal effect in foliage treatment                               Dose                                                                       No.                                                                              (g/a)                                                                            G H I J K L M N O P a b c d e f                                         __________________________________________________________________________    2  50 2 1 2 1 0 1 0 3 1 3 1 1 0 0 0 0                                         3  50 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0                                         5  50 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0                                         7  50 3 0 0 0 1 1 1 2 2 2 0 0 0 0 0 0                                         8  21 0 0 0 2 0 0 0 0 3 4 0 0 0 0 0 0                                         9  50 3 0 4 3 1 0 5 0 2 5 0 0 0 0 0 1                                         10 50 0 3 0 1 3 3 2 2 2 4 0 0 1 0 0 0                                         11 37 4 4 1 4 3 3 4 5 3 4 1 1 0 1 0 0                                         12 25 1 0 0 0 2 0 1 0 0 0 0 0 0 0 0 0                                         13 25 1 1 0 0 1 0 3 0 0 2 0 0 0 0 0 0                                         14 25 0 0 0 0 0 0 4 0 0 3 0 0 0 0 0 1                                         16 25 0 0 0 3 3 0 0 0 4 3 0 0 0 0 0 0                                         19 25 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0                                         22 25 0 --                                                                              2 2 0 0 0 0 0 3 0 0 0 0 0 0                                         24 25 1 1 3 4 0 2 0 0 5 5 0 0 0 0 0 2                                         101                                                                              50 3 2 3 4 3 2 2 3 3 4 1 2 1 2 1 1                                         102                                                                              16 0 0 0 0 0 0 1 0 0 1 0 0 0 0 0 0                                         103                                                                              25 5 4 3 5 2 5 3 3 4 4 1 2 1 3 1 2                                         104                                                                              50 9 2 0 0 3 3 2 1 3 1 0 0 0 0 0 0                                         105                                                                              50 5 5 0 5 3 3 5 3 5 5 3 0 0 1 1 4                                         106                                                                              50 4 3 5 5 4 5 3 5 5 4 4 1 3 3 0 5                                         108                                                                              50 3 3 3 4 2 0 2 0 4 4 0 0 1 0 0 1                                         109                                                                              50 3 2 0 0 0 0 3 2 3 4 0 0 0 0 0 0                                         110                                                                              15 3 5 2 3 3 1 3 3 3 4 1 1 1 0 0 0                                         111                                                                              25 4 4 3 3 3 3 3 4 3 3 1 1 1 2 1 0                                         112                                                                              25 4 4 3 3 3 2 3 4 3 3 1 1 1 1 1 0                                         114                                                                              25 4 5 4 4 4 5 4 5 4 4 1 2 0 3 1 2                                         116                                                                              25 4 3 0 3 3 5 3 5 5 3 0 0 0 1 0 1                                         117                                                                              25 0 0 0 2 0 0 0 --                                                                              5 0 0 0 0 0 0 0                                         118                                                                              25 5 0 0 4 4 0 4 --                                                                              3 0 1 0 0 0 0 0                                         119                                                                              25 5 8 0 4 3 2 4 3 5 5 4 1 2 2 1 3                                         121                                                                              25 0 0 0 0 0 0 0 0 4 4 0 0 0 0 0 2                                         122                                                                              25 2 2 0 3 0 2 2 4 0 3 1 0 2 0 0 0                                         123                                                                              25 3 3 3 4 3 2 2 1 5 5 2 2 1 1 0 2                                         124                                                                              25 5 4 2 4 3 3 3 2 5 5 3 3 1 2 1 2                                         __________________________________________________________________________

                  TABLE 5-5                                                       ______________________________________                                        Test on the dwarfing effects in foliage treatment                                            Plant length   Plant age in leaf number                        Compound                                                                              Dose   (cm)           (Leaf stage)                                    No.     (g/a)  A     B     C   D    A   B     C   D                           ______________________________________                                        1       0.1    37    29    15  15   5.5 4.6   5.5 3.5                                 0.4    30    28    15  14   5.0 4.6   5.5 3.5                                 1.6    30    26    15  10   5.0 4.6   5.5 3.5                                 6.3    25    25    12   8   5.2 4.5   6.0 3.8                                 25     17    23     8   5   5.5 4.6   6.0 3.8                         Non-treated                                                                           --     36    30    17  15   5.5 4.6   5.5 3.5                         area                                                                          ______________________________________                                    

                  TABLE 5-6                                                       ______________________________________                                        Test on the dwarfing effects under submerged conditions                                         Plant length                                                                            Plant age in leaf number                          Compound  Dose    (cm)      (Leaf stage)                                      No.       (g/a)   E         E                                                 ______________________________________                                        1         0.01    51        5.7                                                         0.1     51        5.8                                                         1       47        5.6                                                         10      37        5.5                                               Non-treated                                                                             --      53        5.5                                               area                                                                          ______________________________________                                    

                  TABLE 5-7                                                       ______________________________________                                        Test on the dwarfing effects in foliage treatment                                        Plant          Plant age in leaf                                   Dose       length (cm)    number (Leaf stage)                                 No.     (g/a)  A     B    C   D   E   A   B   C    D   E                      ______________________________________                                        101     1.6    14    4.5  41  22  24  5.5 3.5 4.5  2.1 5.0                            6.3    11    3    33  18  21  5.5 3.5 5.5  2.2 5.0                            25      3    1.5  22  13  20  5.5 3.5 4.0  2.0 4.8                    Non-treated                                                                           --     22    14   33  18  23  5.5 3.5 4.5  2.0 5.0                    area                                                                          ______________________________________                                    

                  TABLE 5-8                                                       ______________________________________                                        Test on the dwarfing effects in foliage treatment                             Com-         Plant           Plant age in leaf                                pound Dose   length (cm)     number (Leaf stage)                              No.   (g/a)  A     B   C   D   E   F   A   B   C   D                                                     E   F                                              ______________________________________                                        103   1.6    11     4  25  11  25  25  5.5 4.3 3.0 1.8                                                   5.0 4.8                                                                           6.3  6  3 15  9 22 20 5.3 2.5 3.0 1.2 5.0 4                                   .5                                                                        Non-                                                                              -- 14 15 26 12 26 34 6.0 5.0 3.2 1.8 5.3 4.                                   8                                                                         treated                                                                       area                                               ______________________________________                                    

We claim:
 1. A pyrimidine compound of the formula (1): ##STR178##wherein: R¹ is C₁ -C₆ haloalkyl, C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkylsubstituted by lower alkyl, C₃ -C₆ halocycloalkyl or phenyl substitutedby halogen, C₁ -C₄ alkoxy, C₁ -C₃ haloalkyl, C₁ -C₃ haloalkoxy orphenyl;R² is hydrogen, C₁ -C₆ alkyl, C₃ -C₆ cycloalkyl, C₃ -C₆cycloalkyl (C₁ -C₄)alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ halocycloalkyl, C₃-C₈ alkenyl, C₃ -C₈ alkynyl, C₁ -C₂ sulfonyl (C₁ -C₄)alkyl, C₄alkylthiol (C₃ -C₆)cycloalkyl, phenyl or phenyl substituted by halogen,C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkyl, C₁ -C₃ haloalkoxy orphenyl; and X is carbonyl or --C(R3)OH where R3 is hydrogen, C₁ -C₆alkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkonyl, phenyl or phenyl substituted byhalogen, C₁ --C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkyl, C₁ -C₃haloalkoxy or phenyl; with the proviso that when the carbon atom is anoptically active carbon the racemic mixture and both the optical isomersthereof are included.
 2. The pyrimidine compound of claim 1, which hasone of the following formulae: ##STR179## wherein R2 is selected fromthe group consisting of methyl, ethyl, propyl, isopropyl, cyclopropyl,butyl, sec-butyl, iso-butyl, tert-butyl, cyclobutyl, pentyl, neo-pentyl,iso-pentyl, cyclopentyl, hexyl, cyclohexyl, fluoromethyl,trifluoromethyl, trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,2-fluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl,2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl,3-methoxyphenyl, 4-methoxyphenyl, 2-trifluoromethoxyphenyl,3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-bromophenol,3-bromophenol, 4-bromophenol, 2,4-dichlorophenyl, 3,4-dichlorophenyl,2,6-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,4-difluorophenyl,3,4-difluorophenyl, 2,5-dichlorophenyl, 2,3-dichlorophenyl,2,6-difluorophenyl, bromomethyl, 3,5-dichlorophenyl,2-methyl-4-chlorophenyl, 2-methyl-4-fluorophenyl, 1-methylsulfonylethyl,1-methylcyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl,1-thiomethylcyclopropyl, 1-thioethylcyclopropyl, chloromethyl, CF(Me)₂,1-cyclopropylethyl, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH(Me)C.tbd.CH, C(Me)₂C.tbd.CH, CH(Me)CH═CH₂, 2-tert-butylphenyl, 3-tert-butylphenyl,4-tert-butylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl,2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-butylphenyl,3-butylphenyl, 4-butylphenyl, 2-ethoxyphenyl, 2-isopropoxyphenyl and2-propoxyphenyl.
 3. The pyrimidine compound of claim 1, which has one ofthe following formulae: ##STR180## wherein R2 is selected from the groupconsisting of methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl,sec-butyl, iso-butyl, tert-butyl, cyclobutyl, pentyl, neo-pentyl,iso-pentyl, cyclopentyl, hexyl, cyclohexyl, fluoromethyl,trifluoromethyl, trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,2-fluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl,2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl,3-methoxyphenyl, 4-methoxyphenyl, 2-trifluoromethoxyphenyl,3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-bromophenol,3-bromophenol, 4-bromophenol, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,4-difluorophenyl,3,4-difluorophenyl, 2,5-dichlorophenyl, 2,3-dichlorophenyl,2,6-difluorophenyl, bromomethyl, 3,5-dichlorophenyl,2-methyl-4-chlorophenyl, 2-methyl-4-fluorophenyl, 1-methylsulfonylethyl,1-methylcyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl,1-thiomethylcyclopropyl, 1-thioethylcyclopropyl, chloromethyl, CF(Me)₂,1-cyclopropylethyl, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH(Me)C.tbd.CH, C(Me)₂C.tbd.CH, CH(Me)CH═CH₂, 2-tert-butylphenyl, 3-tert-butylphenyl,4-tert-butylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl,2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-butylphenyl,3-butylphenyl, 4-butylphenyl, 2-ethoxyphenyl, 2-isopropoxyphenyl and2-propoxyphenyl.
 4. The pyrimidine compound of claim 1, which has one ofthe following formulae: ##STR181## wherein R2 is selected from the groupconsisting of methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl,sec-butyl, iso-butyl, tert-butyl, cyclobutyl, pentyl, neo-pentyl,iso-pentyl, cyclopentyl, hexyl, cyclohexyl, fluoromethyl,trifluoromethyl, trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,2-fluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl,2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-methoxyphenyl,3-methoxyphenyl, 4-methoxyphenyl, 2-trifluoromethoxyphenyl,3-trifluoromethoxyphenyl, 4-trifluoromethoxyphenyl, 2-bromophenol,3-bromophenol, 4-bromophenol, 2,4-dichlorophenyl, 3,4-dichlorophenyl,2,6-dichlorophenyl, 2-fluoro-4-chlorophenyl, 2,4-difluorophenyl,3,4-difluorophenyl, 2,5-dichlorophenyl, 2,3-dichlorophenyl,2,6-difluorophenyl, bromomethyl, 3,5-dichlorophenyl,2-methyl-4-chlorophenyl, 2-methyl-4-fluorophenyl, 1-methylsulfonylethyl,1-methylcyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl,1-thiomethylcyclopropyl, 1-thioethylcyclopropyl, chloromethyl, CF(Me)₂,1-cyclopropylethyl, CH₂ CH═CH₂, CH₂ C.tbd.CH, CH(Me)C.tbd.CH, C(Me)₂C.tbd.CH, CH(Me)CH═CH₂, 2-tert-butylphenyl, 3-tert-butylphenyl,4-tert-butylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl,2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-butylphenyl,3-butylphenyl, 4-butylphenyl, 2-ethoxyphenyl, 2-isopropoxyphenyl and2-propoxyphenyl.
 5. A herbicidal composition, comprising:a) one or moreof the pyrimidine compounds of claim 1, and b) a suitable carrier.
 6. Amethod of controlling weed growth, which comprises applying an effectiveamount of the pyrimidine compound of claim 1, on weeds or on soilcontaining weeds.
 7. A method of controlling plant growth, whichcomprises applying an effective amount of the pyrimidine compound ofclaim 1, to a plant in need thereof or on soil containing the same. 8.The method of claim 7, wherein said plant growth control comprisesinhibiting the growth of lawn grass.
 9. The method of claim 7, whereinsaid plant growth control comprises controlling fruit tree turions. 10.The method of claim 7, wherein said plant growth control comprisesdwarfing ornamental plants.
 11. The method of claim 7, wherein saidplant growth control comprises suppressing the growth of hedge plants.12. The method of claim 7, wherein said plant growth control comprisescontrolling flowering of a plant.